NPASS Compound

Structure

CID33068 OpenBabel06191715362D 87 96 0 0 1 0 0 0 0 0999 V2000 4.1459 -8.2278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5172 -5.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3730 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 0.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3730 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2280 -0.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7452 -4.6286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3995 -7.2816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4290 -5.7107 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8484 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 3.4286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4816 0.0346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9987 -3.6824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8484 1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5451 1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8484 -1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3457 -7.0281 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1217 -6.4033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4278 0.2881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9385 1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5992 -6.0819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0679 -6.1498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7868 1.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1204 -0.4046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0901 1.9592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3598 -3.2432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3060 -2.9897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7868 2.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9065 -5.3892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3214 -5.2036 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3934 2.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6352 3.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8669 -1.3508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1063 -4.1894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0901 2.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9603 -5.6427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6288 -4.5109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8832 1.1108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 -2.8720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 1.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8484 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3934 1.9592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6967 -0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 4.4082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7889 0.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9449 -3.4288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -2.4490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0384 -7.7208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8682 -7.3495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6813 1.2343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9385 0.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5454 -5.8283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7606 -6.8425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6352 1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0667 -0.1510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6672 -2.5505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6352 4.4082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4835 2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8628 1.1108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 0.2625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2434 -3.1256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9207 -1.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7990 -4.8821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7068 -6.5889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6826 -4.7644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5596 -2.0435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9385 3.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1601 -4.4430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2677 -4.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 3.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8823 -3.5647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 53 1 0 0 0 0 4 53 1 0 0 0 0 6 55 1 0 0 0 0 9 10 1 0 0 0 0 9 22 2 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 55 1 0 0 0 0 13 14 1 0 0 0 0 13 53 1 0 0 0 0 14 58 1 0 0 0 0 15 23 1 0 0 0 0 15 53 1 0 0 0 0 16 24 1 0 0 0 0 16 54 1 0 0 0 0 17 29 1 0 0 0 0 17 56 1 0 0 0 0 18 25 1 0 0 0 0 18 78 1 0 0 0 0 19 26 1 0 0 0 0 19 79 1 0 0 0 0 20 1 1 6 0 0 0 20 30 1 0 0 0 0 20 80 1 0 0 0 0 21 2 1 6 0 0 0 21 31 1 0 0 0 0 21 81 1 0 0 0 0 22 23 1 0 0 0 0 22 56 1 0 0 0 0 23 58 1 6 0 0 0 24 44 1 0 0 0 0 24 59 1 1 0 0 0 25 32 1 0 0 0 0 25 60 1 1 0 0 0 26 40 1 0 0 0 0 26 61 1 6 0 0 0 27 54 1 1 0 0 0 27 55 1 0 0 0 0 28 54 1 1 0 0 0 28 57 1 0 0 0 0 29 58 1 6 0 0 0 29 62 1 0 0 0 0 30 34 1 0 0 0 0 30 63 1 1 0 0 0 31 35 1 0 0 0 0 31 64 1 1 0 0 0 32 37 1 0 0 0 0 32 65 1 6 0 0 0 33 36 1 0 0 0 0 33 38 1 0 0 0 0 33 66 1 1 0 0 0 34 42 1 0 0 0 0 34 67 1 6 0 0 0 35 43 1 0 0 0 0 35 68 1 6 0 0 0 36 41 1 0 0 0 0 36 69 1 6 0 0 0 37 46 1 0 0 0 0 37 70 1 1 0 0 0 38 48 1 0 0 0 0 38 71 1 6 0 0 0 39 40 1 0 0 0 0 39 47 1 0 0 0 0 39 72 1 6 0 0 0 40 82 1 1 0 0 0 41 45 1 1 0 0 0 41 83 1 0 0 0 0 42 49 1 0 0 0 0 42 84 1 6 0 0 0 43 50 1 0 0 0 0 43 85 1 6 0 0 0 44 57 1 1 0 0 0 44 86 1 0 0 0 0 45 73 2 0 0 0 0 45 74 1 0 0 0 0 46 78 1 0 0 0 0 46 82 1 6 0 0 0 47 79 1 0 0 0 0 47 84 1 1 0 0 0 48 83 1 0 0 0 0 48 86 1 1 0 0 0 49 80 1 0 0 0 0 49 85 1 1 0 0 0 50 81 1 0 0 0 0 50 87 1 1 0 0 0 51 57 1 0 0 0 0 51 75 2 0 0 0 0 51 76 1 0 0 0 0 52 77 2 0 0 0 0 52 87 1 0 0 0 0 54 5 1 1 0 0 0 55 56 1 6 0 0 0 56 7 1 6 0 0 0 57 8 1 1 0 0 0 58 52 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1250.56
Volume:	1170.53
LogP:	-0.285
LogD:	0.269
LogS:	-2.518
# Rotatable Bonds:	13
TPSA:	467.19
# H-Bond Aceptor:	29
# H-Bond Donor:	16
# Rings:	10
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.463
Fsp3:	0.914
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.833
MDCK Permeability:	0.0004630704061128199
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	47.47439956665039%
Volume Distribution (VD):	-0.0
Pgp-substrate:	20.020681381225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.521
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.049
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.536

Download Data

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

Natural Product: NPC33068

Natural Product ID:	NPC33068
*Common Name:**	Zanhasaponin C
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(2S,3R,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-4-carboxy-8a-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxycarbonyl-2,8-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:	Zanhasaponin C
Standard InCHIKey:	DPBXIHJKNCYHRH-QDKXBJSSSA-N
Standard InCHI:	InChI=1S/C58H90O29/c1-20-30(63)34(67)42(84-47-39(72)40(26(61)19-79-47)82-46-37(70)32(65)25(60)18-78-46)49(80-20)85-43-35(68)31(64)21(2)81-50(43)87-52(77)58-14-13-53(3,4)15-23(58)22-9-10-27-54(5)16-24(59)44(86-48-38(71)33(66)36(69)41(83-48)45(73)74)57(8,51(75)76)28(54)11-12-55(27,6)56(22,7)17-29(58)62/h9,20-21,23-44,46-50,59-72H,10-19H2,1-8H3,(H,73,74)(H,75,76)/t20-,21-,23-,24-,25+,26+,27+,28+,29+,30-,31-,32-,33-,34+,35+,36-,37+,38+,39+,40-,41-,42+,43+,44-,46-,47-,48-,49-,50-,54+,55+,56+,57-,58+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@](C)([C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506739
PubChem CID:	44593351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051916]
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	root bark	n.a.	n.a.	PMID[9392883]
NPO25719	Eria aurantiaca	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23090	Eperua leucantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	30.0	%	PMID[525285]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	79.0	ug	PMID[525284]

☑ 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 NPC33068 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	287
0.1-0.2	1985
0.2-0.3	5423
0.3-0.4	10446
0.4-0.5	11143
0.5-0.6	6931
0.6-0.7	3726
0.7-0.8	1794
0.8-0.85	382
0.85-0.9	101
0.9-0.95	356
0.95-1	123

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC200049
0.9912	High Similarity	NPC258617
0.9912	High Similarity	NPC302543
0.9912	High Similarity	NPC283417
0.9912	High Similarity	NPC257211
0.9825	High Similarity	NPC4749
0.9825	High Similarity	NPC80986
0.9825	High Similarity	NPC21691
0.9825	High Similarity	NPC213952
0.9825	High Similarity	NPC131469
0.9825	High Similarity	NPC236870
0.9825	High Similarity	NPC187290
0.9825	High Similarity	NPC475591
0.9825	High Similarity	NPC313110
0.9825	High Similarity	NPC10607
0.9741	High Similarity	NPC284449
0.9741	High Similarity	NPC475368
0.9741	High Similarity	NPC470218
0.9737	High Similarity	NPC31838
0.9737	High Similarity	NPC86222
0.9737	High Similarity	NPC62725
0.9737	High Similarity	NPC22956
0.9737	High Similarity	NPC187618
0.9737	High Similarity	NPC104372
0.9737	High Similarity	NPC11242
0.9737	High Similarity	NPC301449
0.9737	High Similarity	NPC64715
0.9737	High Similarity	NPC114484
0.9737	High Similarity	NPC159309
0.9737	High Similarity	NPC222580
0.9737	High Similarity	NPC171544
0.9737	High Similarity	NPC302887
0.9737	High Similarity	NPC297263
0.9737	High Similarity	NPC223301
0.9655	High Similarity	NPC160452
0.9655	High Similarity	NPC23275
0.9652	High Similarity	NPC162574
0.9649	High Similarity	NPC118440
0.9649	High Similarity	NPC236657
0.9573	High Similarity	NPC181066
0.9573	High Similarity	NPC469947
0.9569	High Similarity	NPC44716
0.9569	High Similarity	NPC235405
0.9569	High Similarity	NPC281148
0.9569	High Similarity	NPC30735
0.9569	High Similarity	NPC2370
0.9561	High Similarity	NPC180550
0.9561	High Similarity	NPC192791
0.9561	High Similarity	NPC39211
0.9561	High Similarity	NPC472949
0.9561	High Similarity	NPC309780
0.9561	High Similarity	NPC469945
0.9561	High Similarity	NPC475171
0.9561	High Similarity	NPC114441
0.9561	High Similarity	NPC157868
0.9561	High Similarity	NPC35405
0.9561	High Similarity	NPC6377
0.9561	High Similarity	NPC214484
0.9561	High Similarity	NPC208381
0.9561	High Similarity	NPC473884
0.9561	High Similarity	NPC11551
0.9487	High Similarity	NPC471962
0.9487	High Similarity	NPC247315
0.9487	High Similarity	NPC470477
0.9487	High Similarity	NPC471963
0.9483	High Similarity	NPC235438
0.9483	High Similarity	NPC107966
0.9483	High Similarity	NPC249848
0.9483	High Similarity	NPC40775
0.9474	High Similarity	NPC237191
0.9474	High Similarity	NPC286347
0.9412	High Similarity	NPC470475
0.9412	High Similarity	NPC470476
0.9402	High Similarity	NPC478066
0.9402	High Similarity	NPC262199
0.9402	High Similarity	NPC471964
0.9402	High Similarity	NPC14617
0.9402	High Similarity	NPC202666
0.9402	High Similarity	NPC471961
0.9397	High Similarity	NPC242840
0.9397	High Similarity	NPC75417
0.9397	High Similarity	NPC31193
0.9391	High Similarity	NPC471577
0.9386	High Similarity	NPC475209
0.9386	High Similarity	NPC102505
0.9386	High Similarity	NPC220160
0.9386	High Similarity	NPC286457
0.9386	High Similarity	NPC475514
0.9386	High Similarity	NPC191827
0.9386	High Similarity	NPC300419
0.9386	High Similarity	NPC473824
0.9386	High Similarity	NPC123522
0.9386	High Similarity	NPC85154
0.9386	High Similarity	NPC104137
0.9386	High Similarity	NPC33012
0.9386	High Similarity	NPC475119
0.9386	High Similarity	NPC473452
0.9386	High Similarity	NPC8524
0.9386	High Similarity	NPC224121
0.9386	High Similarity	NPC309223
0.9386	High Similarity	NPC69811
0.9386	High Similarity	NPC470876
0.9339	High Similarity	NPC476776
0.9316	High Similarity	NPC471965
0.931	High Similarity	NPC294112
0.931	High Similarity	NPC476991
0.9304	High Similarity	NPC109588
0.9304	High Similarity	NPC470513
0.9304	High Similarity	NPC470514
0.9298	High Similarity	NPC305267
0.9298	High Similarity	NPC26626
0.9298	High Similarity	NPC288205
0.9298	High Similarity	NPC37134
0.9298	High Similarity	NPC51465
0.9298	High Similarity	NPC476992
0.9298	High Similarity	NPC75287
0.9298	High Similarity	NPC291903
0.9256	High Similarity	NPC476775
0.9256	High Similarity	NPC476780
0.9256	High Similarity	NPC476774
0.9256	High Similarity	NPC271610
0.9244	High Similarity	NPC285091
0.9231	High Similarity	NPC68767
0.9231	High Similarity	NPC275225
0.9231	High Similarity	NPC51099
0.9231	High Similarity	NPC293031
0.9224	High Similarity	NPC135849
0.9224	High Similarity	NPC51564
0.9224	High Similarity	NPC207738
0.9224	High Similarity	NPC25663
0.9224	High Similarity	NPC473386
0.9217	High Similarity	NPC110633
0.9217	High Similarity	NPC148417
0.9217	High Similarity	NPC136768
0.9217	High Similarity	NPC471580
0.9211	High Similarity	NPC79643
0.9211	High Similarity	NPC305981
0.9211	High Similarity	NPC469782
0.9211	High Similarity	NPC294453
0.9211	High Similarity	NPC57484
0.9211	High Similarity	NPC70809
0.9211	High Similarity	NPC41061
0.9211	High Similarity	NPC67857
0.9211	High Similarity	NPC473714
0.9211	High Similarity	NPC164389
0.9211	High Similarity	NPC475486
0.9211	High Similarity	NPC261506
0.9211	High Similarity	NPC204414
0.9211	High Similarity	NPC71065
0.9211	High Similarity	NPC298034
0.9211	High Similarity	NPC476068
0.9211	High Similarity	NPC224381
0.9211	High Similarity	NPC54636
0.9211	High Similarity	NPC60557
0.9211	High Similarity	NPC475140
0.9211	High Similarity	NPC309907
0.9211	High Similarity	NPC43550
0.9211	High Similarity	NPC65105
0.9211	High Similarity	NPC4328
0.9211	High Similarity	NPC471550
0.9211	High Similarity	NPC161717
0.9211	High Similarity	NPC293330
0.9211	High Similarity	NPC202828
0.9211	High Similarity	NPC76972
0.9211	High Similarity	NPC123199
0.9211	High Similarity	NPC227551
0.9211	High Similarity	NPC475160
0.9211	High Similarity	NPC471385
0.9211	High Similarity	NPC100639
0.9211	High Similarity	NPC119592
0.9211	High Similarity	NPC236638
0.9211	High Similarity	NPC250247
0.9187	High Similarity	NPC476778
0.9187	High Similarity	NPC476777
0.918	High Similarity	NPC312650
0.918	High Similarity	NPC277212
0.918	High Similarity	NPC30279
0.918	High Similarity	NPC71391
0.918	High Similarity	NPC178264
0.918	High Similarity	NPC192765
0.918	High Similarity	NPC473918
0.918	High Similarity	NPC46823
0.9174	High Similarity	NPC273878
0.9174	High Similarity	NPC477196
0.9174	High Similarity	NPC97918
0.9174	High Similarity	NPC11577
0.9174	High Similarity	NPC47995
0.9174	High Similarity	NPC88311
0.9174	High Similarity	NPC141600
0.9174	High Similarity	NPC280029
0.9174	High Similarity	NPC470518
0.9174	High Similarity	NPC470912
0.9174	High Similarity	NPC269484
0.9174	High Similarity	NPC305793
0.9174	High Similarity	NPC82380
0.9174	High Similarity	NPC9470
0.9174	High Similarity	NPC252289
0.9174	High Similarity	NPC115656
0.9174	High Similarity	NPC265841
0.9174	High Similarity	NPC107536

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 NPC33068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	2301
0.2-0.3	3844
0.3-0.4	1753
0.4-0.5	565
0.5-0.6	247
0.6-0.7	123
0.7-0.8	37
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9402	High Similarity	NPD8328	Phase 3
0.9217	High Similarity	NPD8295	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7736	Approved
0.7869	Intermediate Similarity	NPD8133	Approved
0.7857	Intermediate Similarity	NPD8516	Approved
0.7857	Intermediate Similarity	NPD8517	Approved
0.7857	Intermediate Similarity	NPD8515	Approved
0.7717	Intermediate Similarity	NPD8513	Phase 3
0.7692	Intermediate Similarity	NPD8293	Discontinued
0.7576	Intermediate Similarity	NPD7319	Approved
0.7519	Intermediate Similarity	NPD6370	Approved
0.7481	Intermediate Similarity	NPD7507	Approved
0.7459	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7492	Approved
0.7377	Intermediate Similarity	NPD6412	Phase 2
0.7364	Intermediate Similarity	NPD8294	Approved
0.7364	Intermediate Similarity	NPD6319	Approved
0.7364	Intermediate Similarity	NPD8377	Approved
0.7364	Intermediate Similarity	NPD6059	Approved
0.7364	Intermediate Similarity	NPD6054	Approved
0.7348	Intermediate Similarity	NPD6616	Approved
0.7317	Intermediate Similarity	NPD6686	Approved
0.7308	Intermediate Similarity	NPD8296	Approved
0.7308	Intermediate Similarity	NPD8335	Approved
0.7308	Intermediate Similarity	NPD8379	Approved
0.7308	Intermediate Similarity	NPD8378	Approved
0.7308	Intermediate Similarity	NPD8380	Approved
0.7293	Intermediate Similarity	NPD7078	Approved
0.7288	Intermediate Similarity	NPD7902	Approved
0.728	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7179	Intermediate Similarity	NPD7748	Approved
0.7176	Intermediate Similarity	NPD6016	Approved
0.7176	Intermediate Similarity	NPD6015	Approved
0.7176	Intermediate Similarity	NPD8033	Approved
0.7132	Intermediate Similarity	NPD6009	Approved
0.7121	Intermediate Similarity	NPD5988	Approved
0.712	Intermediate Similarity	NPD6372	Approved
0.712	Intermediate Similarity	NPD6373	Approved
0.7073	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7900	Approved
0.7023	Intermediate Similarity	NPD7516	Approved
0.7016	Intermediate Similarity	NPD7128	Approved
0.7016	Intermediate Similarity	NPD5739	Approved
0.7016	Intermediate Similarity	NPD6402	Approved
0.7016	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7008	Intermediate Similarity	NPD6650	Approved
0.7008	Intermediate Similarity	NPD6649	Approved
0.6947	Remote Similarity	NPD7328	Approved
0.6947	Remote Similarity	NPD7327	Approved
0.6917	Remote Similarity	NPD6921	Approved
0.6905	Remote Similarity	NPD6899	Approved
0.6905	Remote Similarity	NPD6881	Approved
0.6905	Remote Similarity	NPD7320	Approved
0.6899	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD8130	Phase 1
0.6861	Remote Similarity	NPD6033	Approved
0.6825	Remote Similarity	NPD5701	Approved
0.6825	Remote Similarity	NPD5697	Approved
0.6797	Remote Similarity	NPD7102	Approved
0.6797	Remote Similarity	NPD6883	Approved
0.6797	Remote Similarity	NPD7290	Approved
0.6791	Remote Similarity	NPD7503	Approved
0.6788	Remote Similarity	NPD8074	Phase 3
0.6744	Remote Similarity	NPD6847	Approved
0.6744	Remote Similarity	NPD6617	Approved
0.6744	Remote Similarity	NPD6869	Approved
0.6723	Remote Similarity	NPD8034	Phase 2
0.6723	Remote Similarity	NPD6411	Approved
0.6723	Remote Similarity	NPD8035	Phase 2
0.6719	Remote Similarity	NPD6012	Approved
0.6719	Remote Similarity	NPD6014	Approved
0.6719	Remote Similarity	NPD6013	Approved
0.6691	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6641	Remote Similarity	NPD6011	Approved
0.6617	Remote Similarity	NPD7115	Discovery
0.6615	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6336	Discontinued
0.6589	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6101	Approved
0.6538	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7638	Approved
0.6529	Remote Similarity	NPD6399	Phase 3
0.648	Remote Similarity	NPD7640	Approved
0.648	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD6083	Phase 2
0.6449	Remote Similarity	NPD6067	Discontinued
0.6446	Remote Similarity	NPD7983	Approved
0.6423	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6274	Approved
0.6414	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD7329	Approved
0.64	Remote Similarity	NPD4225	Approved
0.6397	Remote Similarity	NPD7100	Approved
0.6397	Remote Similarity	NPD7101	Approved
0.6393	Remote Similarity	NPD8171	Discontinued
0.6393	Remote Similarity	NPD5778	Approved
0.6393	Remote Similarity	NPD5779	Approved
0.6377	Remote Similarity	NPD8080	Discontinued
0.6371	Remote Similarity	NPD4697	Phase 3
0.6357	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5286	Approved
0.6349	Remote Similarity	NPD4696	Approved
0.6349	Remote Similarity	NPD5285	Approved
0.6349	Remote Similarity	NPD4700	Approved
0.6345	Remote Similarity	NPD8415	Approved
0.6324	Remote Similarity	NPD6335	Approved
0.6312	Remote Similarity	NPD8448	Approved
0.6308	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6909	Approved
0.6304	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD6868	Approved
0.6294	Remote Similarity	NPD8390	Approved
0.6294	Remote Similarity	NPD8391	Approved
0.6294	Remote Similarity	NPD8392	Approved
0.6286	Remote Similarity	NPD8341	Approved
0.6286	Remote Similarity	NPD8342	Approved
0.6286	Remote Similarity	NPD8340	Approved
0.6286	Remote Similarity	NPD8299	Approved
0.6281	Remote Similarity	NPD5328	Approved
0.6276	Remote Similarity	NPD8450	Suspended
0.627	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD3573	Approved
0.6241	Remote Similarity	NPD8451	Approved
0.624	Remote Similarity	NPD5222	Approved
0.624	Remote Similarity	NPD5221	Approved
0.624	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD4768	Approved
0.6231	Remote Similarity	NPD4767	Approved
0.6207	Remote Similarity	NPD8449	Approved
0.6204	Remote Similarity	NPD6314	Approved
0.6204	Remote Similarity	NPD6313	Approved
0.6202	Remote Similarity	NPD5174	Approved
0.6202	Remote Similarity	NPD5175	Approved
0.6198	Remote Similarity	NPD6672	Approved
0.6198	Remote Similarity	NPD5737	Approved
0.619	Remote Similarity	NPD5173	Approved
0.6181	Remote Similarity	NPD5956	Approved
0.6179	Remote Similarity	NPD6079	Approved
0.6172	Remote Similarity	NPD5223	Approved
0.6167	Remote Similarity	NPD3618	Phase 1
0.616	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD8336	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6154	Remote Similarity	NPD8337	Approved
0.6149	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4729	Approved
0.6136	Remote Similarity	NPD4730	Approved
0.6131	Remote Similarity	NPD7799	Discontinued
0.6111	Remote Similarity	NPD7839	Suspended
0.6099	Remote Similarity	NPD7829	Approved
0.6099	Remote Similarity	NPD7830	Approved
0.6098	Remote Similarity	NPD46	Approved
0.6098	Remote Similarity	NPD6698	Approved
0.6096	Remote Similarity	NPD8338	Approved
0.6077	Remote Similarity	NPD4754	Approved
0.6071	Remote Similarity	NPD8444	Approved
0.6071	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.605	Remote Similarity	NPD3669	Approved
0.605	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5249	Phase 3
0.6045	Remote Similarity	NPD5247	Approved
0.6045	Remote Similarity	NPD5251	Approved
0.6045	Remote Similarity	NPD5250	Approved
0.6045	Remote Similarity	NPD5248	Approved
0.6027	Remote Similarity	NPD7260	Phase 2
0.6017	Remote Similarity	NPD1780	Approved
0.6017	Remote Similarity	NPD1779	Approved
0.6016	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD6333	Approved
0.6	Remote Similarity	NPD7625	Phase 1
0.6	Remote Similarity	NPD4786	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6334	Approved
0.5988	Remote Similarity	NPD8368	Discontinued
0.5971	Remote Similarity	NPD7641	Discontinued
0.5966	Remote Similarity	NPD3667	Approved
0.5952	Remote Similarity	NPD5282	Discontinued

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