NPASS Compound

Structure

NPC470450 OpenBabel07101718292D 90100 0 0 1 0 0 0 0 0999 V2000 -1.7932 6.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7932 -7.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3992 2.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8475 4.1733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3992 -3.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8475 -5.1733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3652 2.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8135 3.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3652 -3.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8135 -4.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6909 5.9157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6909 -6.9157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1404 3.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1404 -4.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 -3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0723 2.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0723 -3.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7250 6.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7250 -7.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9497 4.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9497 -5.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3461 -1.8966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2426 4.2426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2426 -5.2426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6049 -0.0694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6049 -0.9306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2767 4.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2767 -5.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5015 3.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5015 -4.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -0.3282 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5708 -0.6718 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2779 0.3789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2779 -1.3789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1745 3.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1745 -4.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0179 5.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0179 -6.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4674 3.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4674 -4.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0191 1.3449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0191 -2.3449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8284 -3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8284 2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0382 2.6897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0382 -3.6897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4662 7.1404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4662 -8.1404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8978 -0.2235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5696 3.7944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5696 -4.7944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 2.5696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7944 -3.5696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8296 -1.2941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8296 0.2941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2438 0.1201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2438 -1.1201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 -2.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0520 5.7262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0520 -6.7262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9157 4.6909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9157 -5.6909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0532 1.6037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -2.6037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7262 2.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7262 -3.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 81 1 0 0 0 0 2 82 1 0 0 0 0 3 11 1 0 0 0 0 3 23 2 0 0 0 0 4 12 2 0 0 0 0 4 23 1 0 0 0 0 5 13 1 0 0 0 0 5 24 2 0 0 0 0 6 14 2 0 0 0 0 6 24 1 0 0 0 0 7 15 1 0 0 0 0 7 25 2 0 0 0 0 8 16 2 0 0 0 0 8 25 1 0 0 0 0 9 17 1 0 0 0 0 9 26 2 0 0 0 0 10 18 2 0 0 0 0 10 26 1 0 0 0 0 11 27 2 0 0 0 0 12 27 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 18 30 1 0 0 0 0 19 31 2 0 0 0 0 19 33 1 0 0 0 0 20 32 2 0 0 0 0 20 34 1 0 0 0 0 21 83 1 0 0 0 0 22 84 1 0 0 0 0 25 53 1 0 0 0 0 26 54 1 0 0 0 0 27 63 1 0 0 0 0 28 64 1 0 0 0 0 29 65 1 0 0 0 0 30 66 1 0 0 0 0 31 55 1 0 0 0 0 31 67 1 0 0 0 0 32 56 1 0 0 0 0 32 68 1 0 0 0 0 33 39 2 0 0 0 0 33 85 1 0 0 0 0 34 40 2 0 0 0 0 34 86 1 0 0 0 0 35 21 1 6 0 0 0 35 43 1 0 0 0 0 35 87 1 0 0 0 0 36 22 1 6 0 0 0 36 44 1 0 0 0 0 36 88 1 0 0 0 0 37 23 1 6 0 0 0 37 41 1 0 0 0 0 37 42 1 0 0 0 0 38 24 1 1 0 0 0 38 41 1 0 0 0 0 38 42 1 0 0 0 0 39 45 1 0 0 0 0 39 47 1 0 0 0 0 40 46 1 0 0 0 0 40 48 1 0 0 0 0 41 59 1 1 0 0 0 42 60 1 6 0 0 0 43 49 1 0 0 0 0 43 69 1 1 0 0 0 44 50 1 0 0 0 0 44 70 1 1 0 0 0 45 55 2 0 0 0 0 45 71 1 0 0 0 0 46 56 2 0 0 0 0 46 72 1 0 0 0 0 47 57 1 0 0 0 0 47 73 2 0 0 0 0 48 58 1 0 0 0 0 48 74 2 0 0 0 0 49 51 1 0 0 0 0 49 75 1 6 0 0 0 50 52 1 0 0 0 0 50 76 1 6 0 0 0 51 61 1 0 0 0 0 51 77 1 1 0 0 0 52 62 1 0 0 0 0 52 78 1 1 0 0 0 53 57 2 0 0 0 0 53 85 1 0 0 0 0 54 58 2 0 0 0 0 54 86 1 0 0 0 0 55 81 1 0 0 0 0 56 82 1 0 0 0 0 57 89 1 0 0 0 0 58 90 1 0 0 0 0 59 79 2 0 0 0 0 59 83 1 0 0 0 0 60 80 2 0 0 0 0 60 84 1 0 0 0 0 61 87 1 0 0 0 0 61 89 1 6 0 0 0 62 88 1 0 0 0 0 62 90 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1248.3
Volume:	1169.638
LogP:	3.887
LogD:	1.847
LogS:	-5.055
# Rotatable Bonds:	18
TPSA:	451.62
# H-Bond Aceptor:	28
# H-Bond Donor:	14
# Rings:	11
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.062
Synthetic Accessibility Score:	6.145
Fsp3:	0.29
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.621
MDCK Permeability:	5.3708254199591465e-06
Pgp-inhibitor:	0.977
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.694
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	91.21503448486328%
Volume Distribution (VD):	0.369
Pgp-substrate:	7.3724188804626465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.371
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.072
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	2.831
Half-life (T1/2):	0.237

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.722
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.854
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: NPC470450

Natural Product ID:	NPC470450
*Common Name:**	Geniculatin
IUPAC Name:	n.a.
Synonyms:	Geniculatin
Standard InCHIKey:	NNBOPQPMWAVYCT-JCCQZUOPSA-N
Standard InCHI:	InChI=1S/C62H56O28/c1-81-55-31(67)19-33-39(45(55)71)47(73)57(53(85-33)25-7-15-29(65)16-8-25)89-61-51(77)49(75)43(69)35(87-61)21-83-59(79)41-37(23-3-11-27(63)12-4-23)42(38(41)24-5-13-28(64)14-6-24)60(80)84-22-36-44(70)50(76)52(78)62(88-36)90-58-48(74)40-34(20-32(68)56(82-2)46(40)72)86-54(58)26-9-17-30(66)18-10-26/h3-20,35-38,41-44,49-52,61-72,75-78H,21-22H2,1-2H3/t35-,36-,37-,38-,41-,42-,43-,44-,49+,50+,51-,52-,61+,62+/m1/s1
SMILES:	COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O[C@@H]1O[C@H](COC(=O)[C@@H]2[C@H](c3ccc(cc3)O)[C@H]([C@H]2c2ccc(cc2)O)C(=O)OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)c(c(c4)O)OC)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037053
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.738	mM	PMID[571017]

☑ 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 NPC470450 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	482
0.1-0.2	2027
0.2-0.3	4469
0.3-0.4	9939
0.4-0.5	8611
0.5-0.6	5115
0.6-0.7	6391
0.7-0.8	4541
0.8-0.85	522
0.85-0.9	449
0.9-0.95	146
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9337	High Similarity	NPC475179
0.9333	High Similarity	NPC470455
0.9333	High Similarity	NPC470451
0.9297	High Similarity	NPC3474
0.9282	High Similarity	NPC104910
0.9282	High Similarity	NPC474093
0.9278	High Similarity	NPC470446
0.9278	High Similarity	NPC470449
0.9278	High Similarity	NPC470447
0.9278	High Similarity	NPC470445
0.9231	High Similarity	NPC64755
0.9231	High Similarity	NPC30011
0.9231	High Similarity	NPC72554
0.9231	High Similarity	NPC97817
0.9227	High Similarity	NPC470713
0.9227	High Similarity	NPC460984
0.9227	High Similarity	NPC470717
0.9227	High Similarity	NPC470416
0.9227	High Similarity	NPC25946
0.9227	High Similarity	NPC470720
0.9227	High Similarity	NPC21359
0.9176	High Similarity	NPC473554
0.9176	High Similarity	NPC470719
0.9176	High Similarity	NPC295625
0.9171	High Similarity	NPC135831
0.9171	High Similarity	NPC162394
0.9171	High Similarity	NPC36138
0.9171	High Similarity	NPC156785
0.9171	High Similarity	NPC297503
0.9171	High Similarity	NPC97119
0.9171	High Similarity	NPC470718
0.9171	High Similarity	NPC241781
0.9167	High Similarity	NPC473571
0.9167	High Similarity	NPC473682
0.9167	High Similarity	NPC470443
0.9167	High Similarity	NPC110941
0.9167	High Similarity	NPC470444
0.9167	High Similarity	NPC126784
0.9167	High Similarity	NPC241423
0.913	High Similarity	NPC93065
0.913	High Similarity	NPC469652
0.913	High Similarity	NPC472720
0.913	High Similarity	NPC472724
0.913	High Similarity	NPC472721
0.913	High Similarity	NPC31208
0.913	High Similarity	NPC160543
0.9121	High Similarity	NPC249560
0.9121	High Similarity	NPC223860
0.9121	High Similarity	NPC275977
0.9121	High Similarity	NPC148710
0.9111	High Similarity	NPC173837
0.9076	High Similarity	NPC290289
0.9076	High Similarity	NPC240200
0.9076	High Similarity	NPC473618
0.9076	High Similarity	NPC223534
0.9076	High Similarity	NPC158214
0.9071	High Similarity	NPC33083
0.9066	High Similarity	NPC473072
0.9066	High Similarity	NPC132111
0.9061	High Similarity	NPC471030
0.9056	High Similarity	NPC470949
0.9056	High Similarity	NPC211532
0.9056	High Similarity	NPC8573
0.9056	High Similarity	NPC472384
0.9056	High Similarity	NPC233994
0.9056	High Similarity	NPC89127
0.9056	High Similarity	NPC169733
0.9056	High Similarity	NPC268533
0.9056	High Similarity	NPC471669
0.9056	High Similarity	NPC472380
0.9056	High Similarity	NPC472382
0.9056	High Similarity	NPC198324
0.9056	High Similarity	NPC473862
0.9056	High Similarity	NPC65563
0.9056	High Similarity	NPC472385
0.9027	High Similarity	NPC187632
0.9027	High Similarity	NPC201814
0.9022	High Similarity	NPC260521
0.9022	High Similarity	NPC65489
0.9022	High Similarity	NPC179947
0.9022	High Similarity	NPC469649
0.9016	High Similarity	NPC75574
0.9011	High Similarity	NPC473071
0.9011	High Similarity	NPC473073
0.9006	High Similarity	NPC217520
0.9006	High Similarity	NPC476620
0.9006	High Similarity	NPC37668
0.9006	High Similarity	NPC476618
0.9006	High Similarity	NPC258044
0.9006	High Similarity	NPC293626
0.9006	High Similarity	NPC113836
0.9006	High Similarity	NPC139571
0.9006	High Similarity	NPC35167
0.9006	High Similarity	NPC476619
0.9006	High Similarity	NPC251417
0.9006	High Similarity	NPC472387
0.9006	High Similarity	NPC477895
0.9006	High Similarity	NPC217387
0.9006	High Similarity	NPC476621
0.9006	High Similarity	NPC476623
0.9006	High Similarity	NPC267680
0.9006	High Similarity	NPC196127
0.9006	High Similarity	NPC476622
0.9006	High Similarity	NPC89052
0.9006	High Similarity	NPC253521
0.9	High Similarity	NPC16194
0.9	High Similarity	NPC43211
0.9	High Similarity	NPC294815
0.9	High Similarity	NPC264735
0.9	High Similarity	NPC135277
0.9	High Similarity	NPC19108
0.9	High Similarity	NPC477848
0.9	High Similarity	NPC115760
0.9	High Similarity	NPC101191
0.9	High Similarity	NPC220173
0.9	High Similarity	NPC473327
0.9	High Similarity	NPC476472
0.9	High Similarity	NPC210094
0.9	High Similarity	NPC49344
0.9	High Similarity	NPC237435
0.9	High Similarity	NPC253685
0.8989	High Similarity	NPC189312
0.8978	High Similarity	NPC471091
0.8978	High Similarity	NPC264302
0.8978	High Similarity	NPC97924
0.8978	High Similarity	NPC40078
0.8973	High Similarity	NPC142291
0.8973	High Similarity	NPC7839
0.8967	High Similarity	NPC111490
0.8967	High Similarity	NPC261623
0.8967	High Similarity	NPC469650
0.8956	High Similarity	NPC192539
0.895	High Similarity	NPC144097
0.895	High Similarity	NPC14187
0.895	High Similarity	NPC61904
0.895	High Similarity	NPC219043
0.895	High Similarity	NPC48984
0.895	High Similarity	NPC292019
0.895	High Similarity	NPC202908
0.895	High Similarity	NPC122467
0.895	High Similarity	NPC472991
0.895	High Similarity	NPC472992
0.8944	High Similarity	NPC24043
0.8944	High Similarity	NPC101026
0.8944	High Similarity	NPC45522
0.8944	High Similarity	NPC42773
0.8944	High Similarity	NPC4390
0.8944	High Similarity	NPC169977
0.8944	High Similarity	NPC204693
0.8944	High Similarity	NPC21666
0.8913	High Similarity	NPC318119
0.8913	High Similarity	NPC231254
0.8913	High Similarity	NPC49690
0.8901	High Similarity	NPC168584
0.8901	High Similarity	NPC120952
0.8895	High Similarity	NPC142996
0.8895	High Similarity	NPC34267
0.8895	High Similarity	NPC81042
0.8895	High Similarity	NPC214621
0.8895	High Similarity	NPC223426
0.8895	High Similarity	NPC102028
0.8889	High Similarity	NPC476405
0.8889	High Similarity	NPC259152
0.8889	High Similarity	NPC254540
0.8889	High Similarity	NPC153755
0.8889	High Similarity	NPC33054
0.8889	High Similarity	NPC190003
0.8889	High Similarity	NPC175107
0.8889	High Similarity	NPC26230
0.8889	High Similarity	NPC117260
0.8889	High Similarity	NPC155877
0.8889	High Similarity	NPC176740
0.8889	High Similarity	NPC172807
0.8889	High Similarity	NPC3583
0.8889	High Similarity	NPC471748
0.8889	High Similarity	NPC134532
0.8889	High Similarity	NPC203259
0.8889	High Similarity	NPC60735
0.8889	High Similarity	NPC211594
0.8889	High Similarity	NPC471725
0.8889	High Similarity	NPC472386
0.8883	High Similarity	NPC477082
0.8871	High Similarity	NPC119094
0.8871	High Similarity	NPC477081
0.8871	High Similarity	NPC477083
0.8871	High Similarity	NPC173872
0.8859	High Similarity	NPC321916
0.8859	High Similarity	NPC35924
0.8859	High Similarity	NPC107987
0.8859	High Similarity	NPC199172
0.8852	High Similarity	NPC179862
0.8852	High Similarity	NPC324742
0.8846	High Similarity	NPC231787
0.884	High Similarity	NPC476374
0.884	High Similarity	NPC51774
0.884	High Similarity	NPC172033
0.884	High Similarity	NPC236191
0.884	High Similarity	NPC472993
0.884	High Similarity	NPC175230
0.884	High Similarity	NPC239549

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 NPC470450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	1057
0.2-0.3	2237
0.3-0.4	2718
0.4-0.5	1749
0.5-0.6	673
0.6-0.7	194
0.7-0.8	95
0.8-0.85	3
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7808	Phase 3
0.9	High Similarity	NPD4338	Clinical (unspecified phase)
0.8944	High Similarity	NPD7251	Discontinued
0.8889	High Similarity	NPD6797	Phase 2
0.8833	High Similarity	NPD7472	Approved
0.8778	High Similarity	NPD7054	Approved
0.8729	High Similarity	NPD7074	Phase 3
0.8611	High Similarity	NPD6166	Phase 2
0.8611	High Similarity	NPD6168	Clinical (unspecified phase)
0.8611	High Similarity	NPD6167	Clinical (unspecified phase)
0.8579	High Similarity	NPD7993	Clinical (unspecified phase)
0.8571	High Similarity	NPD7804	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.8342	Intermediate Similarity	NPD8313	Approved
0.8342	Intermediate Similarity	NPD8312	Approved
0.8325	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD3817	Phase 2
0.8122	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD2801	Approved
0.8066	Intermediate Similarity	NPD5402	Approved
0.8056	Intermediate Similarity	NPD1934	Approved
0.7978	Intermediate Similarity	NPD7075	Discontinued
0.7926	Intermediate Similarity	NPD7228	Approved
0.7923	Intermediate Similarity	NPD3882	Suspended
0.7912	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD8151	Discontinued
0.7892	Intermediate Similarity	NPD5494	Approved
0.7884	Intermediate Similarity	NPD5844	Phase 1
0.7876	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7473	Discontinued
0.7869	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7435	Discontinued
0.7819	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD8455	Phase 2
0.7814	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6559	Discontinued
0.776	Intermediate Similarity	NPD6801	Discontinued
0.776	Intermediate Similarity	NPD7685	Pre-registration
0.7754	Intermediate Similarity	NPD6959	Discontinued
0.7722	Intermediate Similarity	NPD1512	Approved
0.7713	Intermediate Similarity	NPD3787	Discontinued
0.7713	Intermediate Similarity	NPD6232	Discontinued
0.7696	Intermediate Similarity	NPD7871	Phase 2
0.7696	Intermediate Similarity	NPD7870	Phase 2
0.7681	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD7874	Approved
0.768	Intermediate Similarity	NPD5403	Approved
0.766	Intermediate Similarity	NPD7199	Phase 2
0.765	Intermediate Similarity	NPD4380	Phase 2
0.7647	Intermediate Similarity	NPD7698	Approved
0.7647	Intermediate Similarity	NPD7696	Phase 3
0.7647	Intermediate Similarity	NPD7697	Approved
0.7644	Intermediate Similarity	NPD7783	Phase 2
0.7644	Intermediate Similarity	NPD3751	Discontinued
0.7644	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD1653	Approved
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD7819	Suspended
0.7611	Intermediate Similarity	NPD1511	Approved
0.7609	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD6778	Approved
0.7586	Intermediate Similarity	NPD6777	Approved
0.7586	Intermediate Similarity	NPD6779	Approved
0.7586	Intermediate Similarity	NPD6781	Approved
0.7586	Intermediate Similarity	NPD6776	Approved
0.7586	Intermediate Similarity	NPD6782	Approved
0.7586	Intermediate Similarity	NPD6780	Approved
0.7585	Intermediate Similarity	NPD7701	Phase 2
0.7577	Intermediate Similarity	NPD7240	Approved
0.7569	Intermediate Similarity	NPD5401	Approved
0.7553	Intermediate Similarity	NPD6234	Discontinued
0.754	Intermediate Similarity	NPD7768	Phase 2
0.7524	Intermediate Similarity	NPD8320	Phase 1
0.7524	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD6799	Approved
0.7488	Intermediate Similarity	NPD7699	Phase 2
0.7488	Intermediate Similarity	NPD7700	Phase 2
0.7488	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7801	Approved
0.7475	Intermediate Similarity	NPD8434	Phase 2
0.7473	Intermediate Similarity	NPD37	Approved
0.7473	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6599	Discontinued
0.7447	Intermediate Similarity	NPD4966	Approved
0.7447	Intermediate Similarity	NPD4965	Approved
0.7447	Intermediate Similarity	NPD4967	Phase 2
0.7387	Intermediate Similarity	NPD8150	Discontinued
0.7382	Intermediate Similarity	NPD1247	Approved
0.7353	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7316	Intermediate Similarity	NPD3749	Approved
0.7308	Intermediate Similarity	NPD6190	Approved
0.7308	Intermediate Similarity	NPD7680	Approved
0.7283	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD919	Approved
0.726	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD1549	Phase 2
0.7228	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7198	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2796	Approved
0.7072	Intermediate Similarity	NPD1510	Phase 2
0.7065	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3750	Approved
0.7042	Intermediate Similarity	NPD7584	Approved
0.7027	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD6213	Phase 3
0.6957	Remote Similarity	NPD6212	Phase 3
0.6957	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7390	Discontinued
0.6947	Remote Similarity	NPD3226	Approved
0.6944	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1613	Approved
0.694	Remote Similarity	NPD2935	Discontinued
0.6939	Remote Similarity	NPD8127	Discontinued
0.6931	Remote Similarity	NPD7549	Discontinued
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2533	Approved
0.6915	Remote Similarity	NPD2532	Approved
0.6915	Remote Similarity	NPD2534	Approved
0.6906	Remote Similarity	NPD230	Phase 1
0.6906	Remote Similarity	NPD1933	Approved
0.6889	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD7585	Approved
0.6851	Remote Similarity	NPD943	Approved
0.6851	Remote Similarity	NPD1240	Approved
0.6837	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6798	Discontinued
0.6828	Remote Similarity	NPD6674	Discontinued
0.6825	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6355	Discontinued
0.6813	Remote Similarity	NPD447	Suspended
0.6806	Remote Similarity	NPD7583	Approved
0.6793	Remote Similarity	NPD3748	Approved
0.6791	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD8059	Phase 3
0.6784	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3027	Phase 3
0.6776	Remote Similarity	NPD1607	Approved
0.6771	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1551	Phase 2
0.6754	Remote Similarity	NPD920	Approved
0.6749	Remote Similarity	NPD5953	Discontinued
0.6742	Remote Similarity	NPD7930	Approved
0.6739	Remote Similarity	NPD7097	Phase 1
0.6734	Remote Similarity	NPD7229	Phase 3
0.6733	Remote Similarity	NPD7286	Phase 2
0.6722	Remote Similarity	NPD4908	Phase 1
0.6722	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8368	Discontinued
0.6703	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2799	Discontinued
0.6702	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8067	Phase 3
0.6684	Remote Similarity	NPD5353	Approved
0.6683	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8404	Phase 2
0.6682	Remote Similarity	NPD4360	Phase 2
0.6682	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD2800	Approved
0.6649	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3268	Approved
0.6648	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7907	Approved
0.6636	Remote Similarity	NPD8285	Discontinued
0.6631	Remote Similarity	NPD2346	Discontinued
0.663	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5124	Phase 1
0.6622	Remote Similarity	NPD4665	Approved
0.662	Remote Similarity	NPD5006	Approved
0.662	Remote Similarity	NPD5005	Approved
0.6618	Remote Similarity	NPD8407	Phase 2
0.6617	Remote Similarity	NPD5242	Approved
0.6615	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7033	Discontinued
0.6601	Remote Similarity	NPD7799	Discontinued
0.6584	Remote Similarity	NPD2403	Approved
0.6576	Remote Similarity	NPD4060	Phase 1
0.6571	Remote Similarity	NPD8435	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