NPASS Compound

Structure

NPC472721 OpenBabel07101718232D 101111 0 0 1 0 0 0 0 0999 V2000 -10.6603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3923 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4679 2.7252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3337 -5.1397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0008 -6.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3649 -2.4136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3619 -4.9040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2450 -5.5364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1195 3.2860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6154 -6.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 -7.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6718 -5.6277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7000 -5.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9643 3.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9253 -6.8229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1335 -7.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9535 -6.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8892 -6.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6603 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5511 -3.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8632 -4.7503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7942 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7942 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2583 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -6.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8607 4.2519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5872 -6.3350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5673 -7.8280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -5.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5581 3.9307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2071 -7.7824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3227 -8.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3923 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2635 -7.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8342 -7.1725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3923 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -4.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 1.2588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5466 -3.8270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7915 -5.1220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 -1.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1795 -2.9937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9582 -3.7549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 1 20 1 0 0 0 0 2 13 1 0 0 0 0 2 21 2 0 0 0 0 3 14 2 0 0 0 0 3 22 1 0 0 0 0 4 14 1 0 0 0 0 4 23 2 0 0 0 0 5 15 2 0 0 0 0 5 24 1 0 0 0 0 6 15 1 0 0 0 0 6 28 2 0 0 0 0 7 16 2 0 0 0 0 7 25 1 0 0 0 0 8 17 2 0 0 0 0 8 26 1 0 0 0 0 9 18 2 0 0 0 0 9 27 1 0 0 0 0 10 19 2 0 0 0 0 10 29 1 0 0 0 0 11 62 1 0 0 0 0 12 91 1 0 0 0 0 13 53 1 0 0 0 0 14 54 1 0 0 0 0 15 55 1 0 0 0 0 16 32 1 0 0 0 0 16 56 1 0 0 0 0 17 33 1 0 0 0 0 17 57 1 0 0 0 0 18 46 1 0 0 0 0 18 58 1 0 0 0 0 19 47 1 0 0 0 0 19 59 1 0 0 0 0 20 34 2 0 0 0 0 20 63 1 0 0 0 0 21 34 1 0 0 0 0 21 64 1 0 0 0 0 22 35 2 0 0 0 0 22 65 1 0 0 0 0 23 35 1 0 0 0 0 23 66 1 0 0 0 0 24 36 2 0 0 0 0 24 67 1 0 0 0 0 25 37 2 0 0 0 0 25 68 1 0 0 0 0 26 38 2 0 0 0 0 26 69 1 0 0 0 0 27 39 2 0 0 0 0 27 70 1 0 0 0 0 28 36 1 0 0 0 0 28 92 1 0 0 0 0 29 40 2 0 0 0 0 29 93 1 0 0 0 0 30 11 1 1 0 0 0 30 41 1 0 0 0 0 30 94 1 0 0 0 0 31 12 1 6 0 0 0 31 48 1 0 0 0 0 31 95 1 0 0 0 0 32 33 1 0 0 0 0 32 42 2 0 0 0 0 33 43 2 0 0 0 0 34 71 1 0 0 0 0 35 72 1 0 0 0 0 36 73 1 0 0 0 0 37 42 1 0 0 0 0 37 74 1 0 0 0 0 38 43 1 0 0 0 0 38 75 1 0 0 0 0 39 44 1 0 0 0 0 39 76 1 0 0 0 0 40 45 1 0 0 0 0 40 77 1 0 0 0 0 41 49 1 0 0 0 0 41 78 1 6 0 0 0 42 79 1 0 0 0 0 43 80 1 0 0 0 0 44 46 2 0 0 0 0 44 81 1 0 0 0 0 45 47 2 0 0 0 0 45 82 1 0 0 0 0 46 93 1 0 0 0 0 47 92 1 0 0 0 0 48 50 1 0 0 0 0 48 96 1 1 0 0 0 49 51 1 0 0 0 0 49 97 1 1 0 0 0 50 52 1 0 0 0 0 50 98 1 6 0 0 0 51 60 1 0 0 0 0 51 99 1 6 0 0 0 52 61 1 0 0 0 0 52100 1 1 0 0 0 53 83 2 0 0 0 0 53 97 1 0 0 0 0 54 84 2 0 0 0 0 54 98 1 0 0 0 0 55 85 2 0 0 0 0 55101 1 0 0 0 0 56 86 2 0 0 0 0 56 91 1 0 0 0 0 57 87 2 0 0 0 0 57 96 1 0 0 0 0 58 88 2 0 0 0 0 58 99 1 0 0 0 0 59 89 2 0 0 0 0 59100 1 0 0 0 0 60 90 1 0 0 0 0 60 94 1 0 0 0 0 61 95 1 6 0 0 0 61101 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1418.16
Volume:	1247.279
LogP:	1.787
LogD:	1.644
LogS:	-2.03
# Rotatable Bonds:	12
TPSA:	666.08
# H-Bond Aceptor:	40
# H-Bond Donor:	22
# Rings:	11
# Heavy Atoms:	40

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	6.439
Fsp3:	0.197
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.463
MDCK Permeability:	7.547080713266041e-06
Pgp-inhibitor:	0.523
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	92.20561218261719%
Volume Distribution (VD):	0.092
Pgp-substrate:	139.80914306640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	8.14
Half-life (T1/2):	0.98

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.07
Skin Sensitization:	0.964
Carcinogencity:	0.004
Eye Corrosion:	0.003
Eye Irritation:	0.936
Respiratory Toxicity:	0.0

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC472721

Natural Product ID:	NPC472721
*Common Name:**	TVSSZZKVDMITOQ-IWSQHUBESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TVSSZZKVDMITOQ-IWSQHUBESA-N
Standard InCHI:	InChI=1S/C61H46O40/c62-11-30-41(78)49(97-53(83)13-1-20(63)34(71)21(64)2-13)51(60(90)94-30)99-58(88)18-9-27(70)39(76)44(81)46(18)93-29-10-19-47(45(82)40(29)77)92-28-6-15(5-24(67)36(28)73)55(85)101-61-52(100-59(19)89)50(98-54(84)14-3-22(65)35(72)23(66)4-14)48-31(95-61)12-91-56(86)16-7-25(68)37(74)42(79)32(16)33-17(57(87)96-48)8-26(69)38(75)43(33)80/h1-10,30-31,41,48-52,60-82,90H,11-12H2/t30-,31-,41-,48-,49+,50+,51-,52-,60?,61+/m1/s1
SMILES:	C1C2C(C(C3C(O2)OC(=O)C4=CC(=C(C(=C4)OC5=C(C(=C(C=C5C(=O)O3)OC6=C(C(=C(C=C6C(=O)OC7C(C(C(OC7O)CO)O)OC(=O)C8=CC(=C(C(=C8)O)O)O)O)O)O)O)O)O)O)OC(=O)C9=CC(=C(C(=C9)O)O)O)OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581888
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33012	myricaria bracteata	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25918997]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	4730.0	nM	PMID[450157]
NPT35	Others	n.a.		IC50	=	36810.0	nM	PMID[450157]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC472721 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	1933
0.2-0.3	4207
0.3-0.4	9396
0.4-0.5	8441
0.5-0.6	5008
0.6-0.7	5984
0.7-0.8	5598
0.8-0.85	944
0.85-0.9	601
0.9-0.95	84
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93065
1.0	High Similarity	NPC472720
1.0	High Similarity	NPC469652
1.0	High Similarity	NPC31208
1.0	High Similarity	NPC160543
1.0	High Similarity	NPC472724
0.9942	High Similarity	NPC240200
0.9942	High Similarity	NPC223534
0.9942	High Similarity	NPC290289
0.9942	High Similarity	NPC158214
0.9884	High Similarity	NPC469649
0.9884	High Similarity	NPC187632
0.9884	High Similarity	NPC260521
0.9828	High Similarity	NPC40078
0.9828	High Similarity	NPC97924
0.9828	High Similarity	NPC471091
0.9826	High Similarity	NPC261623
0.9826	High Similarity	NPC111490
0.9826	High Similarity	NPC469650
0.9713	High Similarity	NPC477083
0.9713	High Similarity	NPC477081
0.9655	High Similarity	NPC65489
0.9607	High Similarity	NPC3474
0.9605	High Similarity	NPC477082
0.954	High Similarity	NPC231254
0.9538	High Similarity	NPC8940
0.95	High Similarity	NPC174140
0.9497	High Similarity	NPC189312
0.9492	High Similarity	NPC264302
0.948	High Similarity	NPC80956
0.948	High Similarity	NPC472726
0.948	High Similarity	NPC472725
0.9364	High Similarity	NPC297574
0.9364	High Similarity	NPC472723
0.9326	High Similarity	NPC201814
0.9322	High Similarity	NPC269625
0.9322	High Similarity	NPC179947
0.931	High Similarity	NPC476620
0.931	High Similarity	NPC476621
0.931	High Similarity	NPC476622
0.931	High Similarity	NPC476618
0.931	High Similarity	NPC476623
0.931	High Similarity	NPC476619
0.927	High Similarity	NPC119094
0.927	High Similarity	NPC142291
0.927	High Similarity	NPC473618
0.927	High Similarity	NPC173872
0.927	High Similarity	NPC269046
0.927	High Similarity	NPC7839
0.9261	High Similarity	NPC123259
0.9261	High Similarity	NPC129533
0.9213	High Similarity	NPC237202
0.9209	High Similarity	NPC49690
0.92	High Similarity	NPC472387
0.9171	High Similarity	NPC476358
0.9153	High Similarity	NPC476203
0.9148	High Similarity	NPC471030
0.9143	High Similarity	NPC472992
0.9143	High Similarity	NPC472991
0.913	High Similarity	NPC470450
0.9128	High Similarity	NPC470271
0.9128	High Similarity	NPC190204
0.9128	High Similarity	NPC261411
0.9128	High Similarity	NPC43918
0.9128	High Similarity	NPC311389
0.9106	High Similarity	NPC475179
0.9101	High Similarity	NPC472722
0.9096	High Similarity	NPC469371
0.9091	High Similarity	NPC265380
0.908	High Similarity	NPC5786
0.908	High Similarity	NPC67134
0.908	High Similarity	NPC102851
0.908	High Similarity	NPC47140
0.9075	High Similarity	NPC149300
0.9075	High Similarity	NPC95421
0.9075	High Similarity	NPC198125
0.907	High Similarity	NPC175793
0.905	High Similarity	NPC104910
0.905	High Similarity	NPC475220
0.905	High Similarity	NPC221140
0.905	High Similarity	NPC475352
0.905	High Similarity	NPC473686
0.905	High Similarity	NPC474093
0.905	High Similarity	NPC112380
0.905	High Similarity	NPC229817
0.9045	High Similarity	NPC470718
0.9045	High Similarity	NPC97119
0.9045	High Similarity	NPC135831
0.9045	High Similarity	NPC132111
0.9045	High Similarity	NPC297503
0.904	High Similarity	NPC185275
0.9034	High Similarity	NPC67629
0.9034	High Similarity	NPC79736
0.9029	High Similarity	NPC166674
0.9029	High Similarity	NPC172033
0.9029	High Similarity	NPC473550
0.9029	High Similarity	NPC46640
0.9029	High Similarity	NPC219600
0.9029	High Similarity	NPC88560
0.9029	High Similarity	NPC263119
0.9029	High Similarity	NPC175230
0.9029	High Similarity	NPC34436
0.9023	High Similarity	NPC471416
0.9023	High Similarity	NPC181778
0.9023	High Similarity	NPC204937
0.9023	High Similarity	NPC470272
0.9023	High Similarity	NPC34287
0.9023	High Similarity	NPC149011
0.9023	High Similarity	NPC47521
0.9	High Similarity	NPC30011
0.9	High Similarity	NPC72554
0.9	High Similarity	NPC97817
0.9	High Similarity	NPC105591
0.8994	High Similarity	NPC470713
0.8994	High Similarity	NPC470720
0.8994	High Similarity	NPC470451
0.8994	High Similarity	NPC470455
0.8994	High Similarity	NPC21359
0.8994	High Similarity	NPC460984
0.8994	High Similarity	NPC470717
0.8994	High Similarity	NPC318119
0.8994	High Similarity	NPC470416
0.8994	High Similarity	NPC25946
0.8989	High Similarity	NPC164047
0.8989	High Similarity	NPC208797
0.8989	High Similarity	NPC53680
0.8989	High Similarity	NPC470452
0.8989	High Similarity	NPC117668
0.8989	High Similarity	NPC470453
0.8989	High Similarity	NPC470448
0.8989	High Similarity	NPC125352
0.8983	High Similarity	NPC267549
0.8983	High Similarity	NPC471789
0.8977	High Similarity	NPC142996
0.8977	High Similarity	NPC102028
0.8971	High Similarity	NPC65333
0.8971	High Similarity	NPC472386
0.8971	High Similarity	NPC3583
0.8971	High Similarity	NPC259152
0.8971	High Similarity	NPC100251
0.8966	High Similarity	NPC658
0.8966	High Similarity	NPC112755
0.8966	High Similarity	NPC471457
0.8966	High Similarity	NPC197708
0.8966	High Similarity	NPC170675
0.8966	High Similarity	NPC183036
0.8944	High Similarity	NPC87583
0.8944	High Similarity	NPC295625
0.8944	High Similarity	NPC470719
0.8944	High Similarity	NPC473554
0.8939	High Similarity	NPC470446
0.8939	High Similarity	NPC36138
0.8939	High Similarity	NPC470449
0.8939	High Similarity	NPC156785
0.8939	High Similarity	NPC35924
0.8939	High Similarity	NPC473631
0.8939	High Similarity	NPC470447
0.8939	High Similarity	NPC241781
0.8939	High Similarity	NPC293227
0.8939	High Similarity	NPC475662
0.8939	High Similarity	NPC162394
0.8939	High Similarity	NPC199172
0.8939	High Similarity	NPC321916
0.8939	High Similarity	NPC473717
0.8939	High Similarity	NPC470445
0.8933	High Similarity	NPC84494
0.8933	High Similarity	NPC245059
0.8933	High Similarity	NPC324742
0.8927	High Similarity	NPC268533
0.892	High Similarity	NPC98583
0.892	High Similarity	NPC239549
0.892	High Similarity	NPC472993
0.892	High Similarity	NPC51774
0.892	High Similarity	NPC236191
0.892	High Similarity	NPC204693
0.892	High Similarity	NPC163165
0.8914	High Similarity	NPC44558
0.8914	High Similarity	NPC21190
0.8914	High Similarity	NPC476365
0.8914	High Similarity	NPC183357
0.8914	High Similarity	NPC52353
0.8914	High Similarity	NPC224462
0.8914	High Similarity	NPC22195
0.8914	High Similarity	NPC474434
0.8908	High Similarity	NPC298847
0.8908	High Similarity	NPC31034
0.8908	High Similarity	NPC249977
0.8908	High Similarity	NPC473818
0.8908	High Similarity	NPC45400
0.8895	High Similarity	NPC291957
0.8895	High Similarity	NPC14030
0.8889	High Similarity	NPC275977
0.8889	High Similarity	NPC223860
0.8889	High Similarity	NPC249560
0.8883	High Similarity	NPC170203
0.8876	High Similarity	NPC258044
0.8876	High Similarity	NPC37668
0.8876	High Similarity	NPC267680
0.8876	High Similarity	NPC113836
0.8876	High Similarity	NPC475261

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC472721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1009
0.2-0.3	2112
0.3-0.4	2690
0.4-0.5	1772
0.5-0.6	799
0.6-0.7	242
0.7-0.8	101
0.8-0.85	14
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD7074	Phase 3
0.8807	High Similarity	NPD7472	Approved
0.8764	High Similarity	NPD4338	Clinical (unspecified phase)
0.8757	High Similarity	NPD7993	Clinical (unspecified phase)
0.875	High Similarity	NPD7054	Approved
0.8715	High Similarity	NPD8313	Approved
0.8715	High Similarity	NPD8312	Approved
0.8681	High Similarity	NPD8397	Clinical (unspecified phase)
0.8659	High Similarity	NPD7808	Phase 3
0.8605	High Similarity	NPD4868	Clinical (unspecified phase)
0.8603	High Similarity	NPD7251	Discontinued
0.8588	High Similarity	NPD3818	Discontinued
0.8547	High Similarity	NPD6797	Phase 2
0.8475	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD6166	Phase 2
0.8436	Intermediate Similarity	NPD5844	Phase 1
0.8402	Intermediate Similarity	NPD8151	Discontinued
0.8387	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1465	Phase 2
0.8343	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD7228	Approved
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD8455	Phase 2
0.8156	Intermediate Similarity	NPD6232	Discontinued
0.8122	Intermediate Similarity	NPD7473	Discontinued
0.8114	Intermediate Similarity	NPD1934	Approved
0.8068	Intermediate Similarity	NPD2801	Approved
0.804	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.804	Intermediate Similarity	NPD7783	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7967	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7819	Suspended
0.7944	Intermediate Similarity	NPD5494	Approved
0.7903	Intermediate Similarity	NPD7240	Approved
0.7901	Intermediate Similarity	NPD7199	Phase 2
0.7889	Intermediate Similarity	NPD6234	Discontinued
0.7886	Intermediate Similarity	NPD1653	Approved
0.788	Intermediate Similarity	NPD3751	Discontinued
0.7877	Intermediate Similarity	NPD7768	Phase 2
0.7868	Intermediate Similarity	NPD7435	Discontinued
0.7857	Intermediate Similarity	NPD3787	Discontinued
0.7833	Intermediate Similarity	NPD7075	Discontinued
0.7833	Intermediate Similarity	NPD3749	Approved
0.7831	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD7870	Phase 2
0.7828	Intermediate Similarity	NPD7871	Phase 2
0.7821	Intermediate Similarity	NPD5402	Approved
0.7821	Intermediate Similarity	NPD3817	Phase 2
0.7809	Intermediate Similarity	NPD37	Approved
0.7807	Intermediate Similarity	NPD7685	Pre-registration
0.7797	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD7698	Approved
0.7778	Intermediate Similarity	NPD7696	Phase 3
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD4965	Approved
0.7778	Intermediate Similarity	NPD7697	Approved
0.7723	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7874	Approved
0.7722	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6779	Approved
0.7716	Intermediate Similarity	NPD6776	Approved
0.7716	Intermediate Similarity	NPD6780	Approved
0.7716	Intermediate Similarity	NPD6781	Approved
0.7716	Intermediate Similarity	NPD6782	Approved
0.7716	Intermediate Similarity	NPD6777	Approved
0.7716	Intermediate Similarity	NPD6778	Approved
0.7711	Intermediate Similarity	NPD7701	Phase 2
0.7667	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD1511	Approved
0.7654	Intermediate Similarity	NPD7411	Suspended
0.7627	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7699	Phase 2
0.7614	Intermediate Similarity	NPD7700	Phase 2
0.7571	Intermediate Similarity	NPD1512	Approved
0.755	Intermediate Similarity	NPD6823	Phase 2
0.7524	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7512	Intermediate Similarity	NPD7801	Approved
0.7512	Intermediate Similarity	NPD7680	Approved
0.7487	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8319	Approved
0.7475	Intermediate Similarity	NPD8320	Phase 1
0.7471	Intermediate Similarity	NPD1549	Phase 2
0.7462	Intermediate Similarity	NPD6535	Approved
0.7462	Intermediate Similarity	NPD6534	Approved
0.743	Intermediate Similarity	NPD5403	Approved
0.7423	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7266	Discontinued
0.7414	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3750	Approved
0.7371	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6799	Approved
0.736	Intermediate Similarity	NPD7390	Discontinued
0.736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6190	Approved
0.7318	Intermediate Similarity	NPD2534	Approved
0.7318	Intermediate Similarity	NPD2533	Approved
0.7318	Intermediate Similarity	NPD5401	Approved
0.7318	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD6599	Discontinued
0.7253	Intermediate Similarity	NPD7458	Discontinued
0.7253	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3926	Phase 2
0.7245	Intermediate Similarity	NPD8434	Phase 2
0.7236	Intermediate Similarity	NPD6213	Phase 3
0.7236	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6212	Phase 3
0.7225	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1510	Phase 2
0.7191	Intermediate Similarity	NPD4628	Phase 3
0.7168	Intermediate Similarity	NPD1613	Approved
0.7168	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2796	Approved
0.7159	Intermediate Similarity	NPD2935	Discontinued
0.7158	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD6674	Discontinued
0.7129	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD919	Approved
0.7126	Intermediate Similarity	NPD1933	Approved
0.7108	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3748	Approved
0.7095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD943	Approved
0.7067	Intermediate Similarity	NPD7584	Approved
0.7062	Intermediate Similarity	NPD5408	Approved
0.7062	Intermediate Similarity	NPD5406	Approved
0.7062	Intermediate Similarity	NPD1551	Phase 2
0.7062	Intermediate Similarity	NPD5404	Approved
0.7062	Intermediate Similarity	NPD5405	Approved
0.7056	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8059	Phase 3
0.7032	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD447	Suspended
0.7016	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD4287	Approved
0.6995	Remote Similarity	NPD7930	Approved
0.6977	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1240	Approved
0.6954	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7549	Discontinued
0.6952	Remote Similarity	NPD7585	Approved
0.6938	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5711	Approved
0.6927	Remote Similarity	NPD2346	Discontinued
0.6927	Remote Similarity	NPD5710	Approved
0.691	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8166	Discontinued
0.6906	Remote Similarity	NPD7003	Approved
0.6905	Remote Similarity	NPD7583	Approved
0.6897	Remote Similarity	NPD3027	Phase 3
0.6893	Remote Similarity	NPD1607	Approved
0.6878	Remote Similarity	NPD5353	Approved
0.6875	Remote Similarity	NPD5006	Approved
0.6875	Remote Similarity	NPD5005	Approved
0.6872	Remote Similarity	NPD7177	Discontinued
0.6865	Remote Similarity	NPD920	Approved
0.6853	Remote Similarity	NPD5953	Discontinued
0.6848	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7286	Phase 2
0.6816	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6273	Approved
0.6804	Remote Similarity	NPD5242	Approved
0.6782	Remote Similarity	NPD6841	Approved
0.6782	Remote Similarity	NPD6843	Phase 3
0.6782	Remote Similarity	NPD6842	Approved
0.6778	Remote Similarity	NPD6100	Approved
0.6778	Remote Similarity	NPD6099	Approved
0.6763	Remote Similarity	NPD4420	Approved
0.6761	Remote Similarity	NPD3764	Approved
0.676	Remote Similarity	NPD7097	Phase 1
0.6758	Remote Similarity	NPD1243	Approved
0.6758	Remote Similarity	NPD2800	Approved
0.6743	Remote Similarity	NPD6832	Phase 2
0.6743	Remote Similarity	NPD4908	Phase 1
0.674	Remote Similarity	NPD2344	Approved
0.6739	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8285	Discontinued
0.6727	Remote Similarity	NPD7907	Approved
0.6723	Remote Similarity	NPD6233	Phase 2
0.6722	Remote Similarity	NPD2799	Discontinued
0.6716	Remote Similarity	NPD8054	Approved
0.6716	Remote Similarity	NPD8053	Approved
0.6702	Remote Similarity	NPD4288	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data