NPASS Compound

Structure

NPC74727 OpenBabel07101718192D 44 48 0 0 1 0 0 0 0 0999 V2000 -1.5180 -4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 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 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4743 -5.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 34 1 0 0 0 0 17 27 1 0 0 0 0 17 35 1 0 0 0 0 18 20 1 0 0 0 0 18 37 2 0 0 0 0 19 38 1 0 0 0 0 21 2 1 1 0 0 0 21 22 1 0 0 0 0 22 35 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 36 1 1 0 0 0 25 19 1 6 0 0 0 25 29 1 0 0 0 0 25 43 1 0 0 0 0 26 34 1 6 0 0 0 26 36 1 0 0 0 0 27 36 1 0 0 0 0 27 39 2 0 0 0 0 28 33 1 0 0 0 0 28 44 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 1 0 0 0 30 31 1 0 0 0 0 30 41 1 6 0 0 0 31 32 1 0 0 0 0 31 42 1 1 0 0 0 32 43 1 0 0 0 0 32 44 1 6 0 0 0 34 35 1 6 0 0 0 35 6 1 1 0 0 0 36 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.4
Volume:	648.206
LogP:	4.519
LogD:	4.222
LogS:	-4.734
# Rotatable Bonds:	8
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	5.466
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
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:	-5.106
MDCK Permeability:	6.762105385860195e-06
Pgp-inhibitor:	0.966
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.345
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	93.4098892211914%
Volume Distribution (VD):	1.935
Pgp-substrate:	3.0687103271484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.326
CYP3A4-inhibitor:	0.506
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	3.574
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.584
Carcinogencity:	0.26
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC74727

Natural Product ID:	NPC74727
*Common Name:**	3Beta-Hydroxycucurbita-5,24(E)-Diene-11-One-26-Al-3-O-Beta-D-Glucopyranoside
IUPAC Name:	(E,6R)-2-methyl-6-[(3S,8S,9R,10R,13R,14S,17R)-4,4,9,13,14-pentamethyl-11-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-2-enal
Synonyms:
Standard InCHIKey:	HSPLIGHIUTWLFK-BPACAZBYSA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-20(18-37)9-8-10-21(2)22-15-16-34(5)26-13-11-23-24(36(26,7)27(39)17-35(22,34)6)12-14-28(33(23,3)4)44-32-31(42)30(41)29(40)25(19-38)43-32/h9,11,18,21-22,24-26,28-32,38,40-42H,8,10,12-17,19H2,1-7H3/b20-9+/t21-,22-,24-,25-,26+,28+,29-,30+,31-,32+,34+,35-,36+/m1/s1
SMILES:	C/C(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@@H](C4(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)[C@]3(C)C(=O)C[C@]12C)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261679
PubChem CID:	90676074
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin 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
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717151]

☑ 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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	0.64	ug.mL-1	PMID[534118]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.78	ug.mL-1	PMID[534118]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.46	ug.mL-1	PMID[534118]

☑ 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 NPC74727 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	240
0.1-0.2	1435
0.2-0.3	4842
0.3-0.4	9483
0.4-0.5	11246
0.5-0.6	6556
0.6-0.7	5207
0.7-0.8	3037
0.8-0.85	558
0.85-0.9	75
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC154856
0.9434	High Similarity	NPC475317
0.9434	High Similarity	NPC52241
0.9352	High Similarity	NPC260665
0.934	High Similarity	NPC246205
0.9266	High Similarity	NPC165439
0.9259	High Similarity	NPC210420
0.9259	High Similarity	NPC474265
0.9259	High Similarity	NPC130427
0.9091	High Similarity	NPC473882
0.9091	High Similarity	NPC474557
0.9065	High Similarity	NPC295389
0.9018	High Similarity	NPC45475
0.9009	High Similarity	NPC279638
0.9	High Similarity	NPC477944
0.8991	High Similarity	NPC285410
0.8991	High Similarity	NPC250481
0.8991	High Similarity	NPC263827
0.8947	High Similarity	NPC202051
0.8899	High Similarity	NPC129340
0.8879	High Similarity	NPC210178
0.887	High Similarity	NPC475431
0.886	High Similarity	NPC308459
0.885	High Similarity	NPC239293
0.8829	High Similarity	NPC62696
0.8829	High Similarity	NPC293038
0.8829	High Similarity	NPC251309
0.8818	High Similarity	NPC269466
0.8807	High Similarity	NPC118225
0.8807	High Similarity	NPC265655
0.8807	High Similarity	NPC8431
0.8783	High Similarity	NPC476675
0.8772	High Similarity	NPC190939
0.8772	High Similarity	NPC197003
0.875	High Similarity	NPC102088
0.875	High Similarity	NPC477580
0.8739	High Similarity	NPC471967
0.8739	High Similarity	NPC477253
0.8739	High Similarity	NPC233003
0.8716	High Similarity	NPC195708
0.8707	High Similarity	NPC28532
0.8704	High Similarity	NPC162033
0.8704	High Similarity	NPC95243
0.8704	High Similarity	NPC63023
0.8696	High Similarity	NPC471406
0.8696	High Similarity	NPC470312
0.8684	High Similarity	NPC475632
0.8684	High Similarity	NPC86020
0.8673	High Similarity	NPC244127
0.8661	High Similarity	NPC178981
0.8649	High Similarity	NPC274833
0.8649	High Similarity	NPC292196
0.8644	High Similarity	NPC47113
0.8644	High Similarity	NPC174367
0.8636	High Similarity	NPC477070
0.8636	High Similarity	NPC477069
0.8611	High Similarity	NPC223741
0.8611	High Similarity	NPC121566
0.8611	High Similarity	NPC100955
0.8609	High Similarity	NPC161738
0.8596	High Similarity	NPC477252
0.8584	High Similarity	NPC475163
0.8583	High Similarity	NPC476966
0.8583	High Similarity	NPC471407
0.8571	High Similarity	NPC473890
0.8571	High Similarity	NPC243728
0.8571	High Similarity	NPC472719
0.8571	High Similarity	NPC207845
0.8559	High Similarity	NPC27551
0.8559	High Similarity	NPC475194
0.8559	High Similarity	NPC318135
0.8559	High Similarity	NPC101450
0.8559	High Similarity	NPC274507
0.8559	High Similarity	NPC114961
0.8545	High Similarity	NPC272576
0.8534	High Similarity	NPC472257
0.8534	High Similarity	NPC129393
0.8534	High Similarity	NPC475187
0.8522	High Similarity	NPC473828
0.8522	High Similarity	NPC473617
0.8509	High Similarity	NPC207637
0.8509	High Similarity	NPC31797
0.85	High Similarity	NPC168899
0.85	High Similarity	NPC245094
0.85	High Similarity	NPC69273
0.85	High Similarity	NPC293623
0.8496	Intermediate Similarity	NPC200944
0.8496	Intermediate Similarity	NPC73455
0.8496	Intermediate Similarity	NPC255017
0.8496	Intermediate Similarity	NPC73986
0.8491	Intermediate Similarity	NPC158088
0.8491	Intermediate Similarity	NPC56071
0.8491	Intermediate Similarity	NPC70733
0.8482	Intermediate Similarity	NPC30397
0.8482	Intermediate Similarity	NPC191763
0.8482	Intermediate Similarity	NPC235841
0.8482	Intermediate Similarity	NPC108748
0.8482	Intermediate Similarity	NPC211798
0.8482	Intermediate Similarity	NPC473481
0.8482	Intermediate Similarity	NPC471243
0.8482	Intermediate Similarity	NPC477073
0.8482	Intermediate Similarity	NPC297208
0.8468	Intermediate Similarity	NPC237503
0.8468	Intermediate Similarity	NPC167383
0.8468	Intermediate Similarity	NPC57362
0.8468	Intermediate Similarity	NPC306746
0.8468	Intermediate Similarity	NPC204407
0.8468	Intermediate Similarity	NPC137917
0.8462	Intermediate Similarity	NPC182900
0.8462	Intermediate Similarity	NPC475182
0.8462	Intermediate Similarity	NPC476544
0.8462	Intermediate Similarity	NPC249553
0.8462	Intermediate Similarity	NPC476543
0.8462	Intermediate Similarity	NPC476672
0.8462	Intermediate Similarity	NPC42675
0.8462	Intermediate Similarity	NPC476545
0.8455	Intermediate Similarity	NPC293512
0.8448	Intermediate Similarity	NPC477071
0.8443	Intermediate Similarity	NPC471855
0.8443	Intermediate Similarity	NPC231240
0.844	Intermediate Similarity	NPC75608
0.844	Intermediate Similarity	NPC221562
0.844	Intermediate Similarity	NPC470885
0.844	Intermediate Similarity	NPC93352
0.844	Intermediate Similarity	NPC187400
0.8435	Intermediate Similarity	NPC309433
0.8426	Intermediate Similarity	NPC136816
0.8426	Intermediate Similarity	NPC94919
0.8426	Intermediate Similarity	NPC154452
0.8426	Intermediate Similarity	NPC272015
0.8421	Intermediate Similarity	NPC220293
0.8421	Intermediate Similarity	NPC116024
0.8411	Intermediate Similarity	NPC282669
0.8411	Intermediate Similarity	NPC473200
0.8411	Intermediate Similarity	NPC7341
0.8407	Intermediate Similarity	NPC116794
0.8407	Intermediate Similarity	NPC100383
0.8407	Intermediate Similarity	NPC46388
0.8407	Intermediate Similarity	NPC37739
0.8407	Intermediate Similarity	NPC128925
0.8407	Intermediate Similarity	NPC256798
0.8403	Intermediate Similarity	NPC473505
0.8393	Intermediate Similarity	NPC174679
0.8393	Intermediate Similarity	NPC102914
0.8393	Intermediate Similarity	NPC269095
0.8393	Intermediate Similarity	NPC110139
0.8393	Intermediate Similarity	NPC279554
0.8393	Intermediate Similarity	NPC476884
0.8393	Intermediate Similarity	NPC136877
0.8393	Intermediate Similarity	NPC476887
0.8393	Intermediate Similarity	NPC476885
0.8393	Intermediate Similarity	NPC199457
0.8393	Intermediate Similarity	NPC75747
0.8393	Intermediate Similarity	NPC127056
0.8393	Intermediate Similarity	NPC476883
0.8393	Intermediate Similarity	NPC108709
0.8393	Intermediate Similarity	NPC270667
0.8393	Intermediate Similarity	NPC474589
0.8393	Intermediate Similarity	NPC475296
0.8393	Intermediate Similarity	NPC476881
0.8393	Intermediate Similarity	NPC476880
0.8393	Intermediate Similarity	NPC68419
0.8393	Intermediate Similarity	NPC476882
0.8393	Intermediate Similarity	NPC90856
0.8393	Intermediate Similarity	NPC7870
0.8393	Intermediate Similarity	NPC56713
0.8393	Intermediate Similarity	NPC164194
0.8393	Intermediate Similarity	NPC29069
0.8393	Intermediate Similarity	NPC78046
0.8393	Intermediate Similarity	NPC59804
0.8393	Intermediate Similarity	NPC476886
0.8393	Intermediate Similarity	NPC220984
0.839	Intermediate Similarity	NPC169816
0.839	Intermediate Similarity	NPC94072
0.839	Intermediate Similarity	NPC156789
0.839	Intermediate Similarity	NPC15918
0.839	Intermediate Similarity	NPC305771
0.8381	Intermediate Similarity	NPC108141
0.8378	Intermediate Similarity	NPC177246
0.8378	Intermediate Similarity	NPC476123
0.8378	Intermediate Similarity	NPC284807
0.8378	Intermediate Similarity	NPC258323
0.8378	Intermediate Similarity	NPC295980
0.8378	Intermediate Similarity	NPC28198
0.8378	Intermediate Similarity	NPC473288
0.8378	Intermediate Similarity	NPC88744
0.8376	Intermediate Similarity	NPC476670
0.8376	Intermediate Similarity	NPC241192
0.8374	Intermediate Similarity	NPC316915
0.8364	Intermediate Similarity	NPC473199
0.8364	Intermediate Similarity	NPC309448
0.8364	Intermediate Similarity	NPC242748
0.8364	Intermediate Similarity	NPC473923
0.8364	Intermediate Similarity	NPC473476
0.8362	Intermediate Similarity	NPC291564
0.8361	Intermediate Similarity	NPC173347
0.8361	Intermediate Similarity	NPC241008
0.8349	Intermediate Similarity	NPC473198
0.8348	Intermediate Similarity	NPC473126
0.8348	Intermediate Similarity	NPC302471

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 NPC74727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1706
0.2-0.3	3993
0.3-0.4	2144
0.4-0.5	580
0.5-0.6	233
0.6-0.7	176
0.7-0.8	101
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8972	High Similarity	NPD6412	Phase 2
0.8333	Intermediate Similarity	NPD7507	Approved
0.8214	Intermediate Similarity	NPD6686	Approved
0.8142	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD7319	Approved
0.8083	Intermediate Similarity	NPD6370	Approved
0.8049	Intermediate Similarity	NPD7736	Approved
0.8017	Intermediate Similarity	NPD8328	Phase 3
0.7917	Intermediate Similarity	NPD6054	Approved
0.7851	Intermediate Similarity	NPD8033	Approved
0.7823	Intermediate Similarity	NPD8293	Discontinued
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7769	Intermediate Similarity	NPD8377	Approved
0.7769	Intermediate Similarity	NPD8294	Approved
0.7769	Intermediate Similarity	NPD6059	Approved
0.775	Intermediate Similarity	NPD7328	Approved
0.775	Intermediate Similarity	NPD7327	Approved
0.7712	Intermediate Similarity	NPD8133	Approved
0.7705	Intermediate Similarity	NPD8379	Approved
0.7705	Intermediate Similarity	NPD6016	Approved
0.7705	Intermediate Similarity	NPD6015	Approved
0.7705	Intermediate Similarity	NPD8378	Approved
0.7705	Intermediate Similarity	NPD8296	Approved
0.7705	Intermediate Similarity	NPD8380	Approved
0.7705	Intermediate Similarity	NPD8335	Approved
0.7705	Intermediate Similarity	NPD7503	Approved
0.7686	Intermediate Similarity	NPD7516	Approved
0.7667	Intermediate Similarity	NPD6009	Approved
0.7667	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7492	Approved
0.7642	Intermediate Similarity	NPD5988	Approved
0.7623	Intermediate Similarity	NPD6319	Approved
0.76	Intermediate Similarity	NPD6616	Approved
0.7581	Intermediate Similarity	NPD6067	Discontinued
0.7563	Intermediate Similarity	NPD4632	Approved
0.754	Intermediate Similarity	NPD7078	Approved
0.7523	Intermediate Similarity	NPD6399	Phase 3
0.7521	Intermediate Similarity	NPD7115	Discovery
0.7436	Intermediate Similarity	NPD6899	Approved
0.7436	Intermediate Similarity	NPD6881	Approved
0.7431	Intermediate Similarity	NPD6079	Approved
0.7429	Intermediate Similarity	NPD4786	Approved
0.7414	Intermediate Similarity	NPD6675	Approved
0.7414	Intermediate Similarity	NPD7128	Approved
0.7414	Intermediate Similarity	NPD6402	Approved
0.7414	Intermediate Similarity	NPD5739	Approved
0.7407	Intermediate Similarity	NPD5328	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD6650	Approved
0.7395	Intermediate Similarity	NPD6649	Approved
0.7373	Intermediate Similarity	NPD6373	Approved
0.7373	Intermediate Similarity	NPD6372	Approved
0.735	Intermediate Similarity	NPD5697	Approved
0.7328	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4697	Phase 3
0.7311	Intermediate Similarity	NPD4634	Approved
0.7311	Intermediate Similarity	NPD6883	Approved
0.7311	Intermediate Similarity	NPD7102	Approved
0.7311	Intermediate Similarity	NPD7290	Approved
0.7297	Intermediate Similarity	NPD7748	Approved
0.729	Intermediate Similarity	NPD3618	Phase 1
0.7288	Intermediate Similarity	NPD7320	Approved
0.7281	Intermediate Similarity	NPD4696	Approved
0.7281	Intermediate Similarity	NPD5285	Approved
0.7281	Intermediate Similarity	NPD5286	Approved
0.7257	Intermediate Similarity	NPD6083	Phase 2
0.7257	Intermediate Similarity	NPD6084	Phase 2
0.7257	Intermediate Similarity	NPD4755	Approved
0.7257	Intermediate Similarity	NPD7902	Approved
0.725	Intermediate Similarity	NPD6869	Approved
0.725	Intermediate Similarity	NPD6617	Approved
0.725	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD3667	Approved
0.7227	Intermediate Similarity	NPD6012	Approved
0.7227	Intermediate Similarity	NPD6014	Approved
0.7227	Intermediate Similarity	NPD6013	Approved
0.7209	Intermediate Similarity	NPD6033	Approved
0.7207	Intermediate Similarity	NPD4202	Approved
0.7203	Intermediate Similarity	NPD5701	Approved
0.7193	Intermediate Similarity	NPD7638	Approved
0.7168	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5222	Approved
0.7168	Intermediate Similarity	NPD5221	Approved
0.7165	Intermediate Similarity	NPD7604	Phase 2
0.7155	Intermediate Similarity	NPD5225	Approved
0.7155	Intermediate Similarity	NPD5224	Approved
0.7155	Intermediate Similarity	NPD5211	Phase 2
0.7155	Intermediate Similarity	NPD4633	Approved
0.7155	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD5983	Phase 2
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD4700	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7119	Intermediate Similarity	NPD6008	Approved
0.7117	Intermediate Similarity	NPD7515	Phase 2
0.7105	Intermediate Similarity	NPD5173	Approved
0.7103	Intermediate Similarity	NPD3665	Phase 1
0.7103	Intermediate Similarity	NPD3666	Approved
0.7103	Intermediate Similarity	NPD3133	Approved
0.7094	Intermediate Similarity	NPD5174	Approved
0.7094	Intermediate Similarity	NPD5175	Approved
0.7091	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD5223	Approved
0.7054	Intermediate Similarity	NPD6336	Discontinued
0.7034	Intermediate Similarity	NPD5141	Approved
0.7008	Intermediate Similarity	NPD8513	Phase 3
0.7008	Intermediate Similarity	NPD8515	Approved
0.7008	Intermediate Similarity	NPD8516	Approved
0.7008	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7900	Approved
0.6975	Remote Similarity	NPD4768	Approved
0.6975	Remote Similarity	NPD4767	Approved
0.6972	Remote Similarity	NPD7334	Approved
0.6972	Remote Similarity	NPD7521	Approved
0.6972	Remote Similarity	NPD6409	Approved
0.6972	Remote Similarity	NPD7146	Approved
0.6972	Remote Similarity	NPD5330	Approved
0.6972	Remote Similarity	NPD6684	Approved
0.697	Remote Similarity	NPD5956	Approved
0.6967	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8034	Phase 2
0.6964	Remote Similarity	NPD8035	Phase 2
0.6942	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5695	Phase 3
0.693	Remote Similarity	NPD4629	Approved
0.693	Remote Similarity	NPD5210	Approved
0.6897	Remote Similarity	NPD5696	Approved
0.6885	Remote Similarity	NPD5250	Approved
0.6885	Remote Similarity	NPD5247	Approved
0.6885	Remote Similarity	NPD5249	Phase 3
0.6885	Remote Similarity	NPD5248	Approved
0.6885	Remote Similarity	NPD5251	Approved
0.688	Remote Similarity	NPD6274	Approved
0.686	Remote Similarity	NPD5128	Approved
0.685	Remote Similarity	NPD7101	Approved
0.685	Remote Similarity	NPD7100	Approved
0.6847	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD8336	Approved
0.6818	Remote Similarity	NPD8337	Approved
0.6818	Remote Similarity	NPD5279	Phase 3
0.6807	Remote Similarity	NPD4754	Approved
0.6789	Remote Similarity	NPD3668	Phase 3
0.6772	Remote Similarity	NPD6335	Approved
0.6759	Remote Similarity	NPD4221	Approved
0.6759	Remote Similarity	NPD4223	Phase 3
0.6754	Remote Similarity	NPD8171	Discontinued
0.6752	Remote Similarity	NPD4225	Approved
0.6748	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6868	Approved
0.6741	Remote Similarity	NPD8449	Approved
0.6727	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5329	Approved
0.6726	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6698	Approved
0.6694	Remote Similarity	NPD5217	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5215	Approved
0.6694	Remote Similarity	NPD5216	Approved
0.6693	Remote Similarity	NPD6317	Approved
0.6691	Remote Similarity	NPD8450	Suspended
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD7641	Discontinued
0.6641	Remote Similarity	NPD6314	Approved
0.664	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6080	Approved
0.6637	Remote Similarity	NPD6904	Approved
0.6637	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD4197	Approved
0.6618	Remote Similarity	NPD8338	Approved
0.6615	Remote Similarity	NPD6909	Approved
0.6615	Remote Similarity	NPD6908	Approved
0.6613	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5135	Approved
0.6613	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD7524	Approved
0.6607	Remote Similarity	NPD3573	Approved
0.6589	Remote Similarity	NPD4522	Approved
0.6585	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5168	Approved
0.6583	Remote Similarity	NPD7632	Discontinued
0.6574	Remote Similarity	NPD7525	Registered
0.6574	Remote Similarity	NPD4695	Discontinued
0.6571	Remote Similarity	NPD7339	Approved
0.6571	Remote Similarity	NPD6942	Approved
0.656	Remote Similarity	NPD5127	Approved
0.6545	Remote Similarity	NPD4788	Approved
0.6544	Remote Similarity	NPD7260	Phase 2
0.6522	Remote Similarity	NPD5284	Approved
0.6522	Remote Similarity	NPD5281	Approved
0.6518	Remote Similarity	NPD4693	Phase 3

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