NPASS Compound

Structure

NPC130427 OpenBabel07101718222D 45 49 0 0 1 0 0 0 0 0999 V2000 -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 1.6984 -3.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 -4.4677 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 -0.5909 -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 -0.9000 -2.9543 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 8.6603 3.0000 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 -0.2308 -3.6974 0.0000 C 0 0 0 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 0.7473 -3.4895 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 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -4.6485 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 1.0563 -2.5385 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 2 32 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 34 1 0 0 0 0 17 26 1 0 0 0 0 17 35 1 0 0 0 0 18 37 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 35 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 0 0 0 0 22 36 1 1 0 0 0 23 18 1 6 0 0 0 23 28 1 0 0 0 0 23 44 1 0 0 0 0 24 34 1 6 0 0 0 24 36 1 0 0 0 0 25 33 1 0 0 0 0 25 38 2 0 0 0 0 26 36 1 0 0 0 0 26 39 2 0 0 0 0 27 32 1 0 0 0 0 27 45 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 1 0 0 0 29 30 1 0 0 0 0 29 41 1 6 0 0 0 30 31 1 0 0 0 0 30 42 1 1 0 0 0 31 44 1 0 0 0 0 31 45 1 6 0 0 0 33 43 1 0 0 0 0 34 35 1 6 0 0 0 35 7 1 1 0 0 0 36 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.41
Volume:	659.632
LogP:	3.848
LogD:	3.67
LogS:	-4.286
# Rotatable Bonds:	8
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	5.419
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.106
MDCK Permeability:	7.949251994432416e-06
Pgp-inhibitor:	0.988
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	81.58330535888672%
Volume Distribution (VD):	0.75
Pgp-substrate:	6.866742134094238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.223
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	4.109
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.098
Carcinogencity:	0.309
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC130427

Natural Product ID:	NPC130427
*Common Name:**	Bryonioside F
IUPAC Name:	(3S,8S,9R,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methyl-5-oxoheptan-2-yl]-4,4,9,13,14-pentamethyl-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-11-one
Synonyms:	bryonioside F
Standard InCHIKey:	IMFAPKVFQZYYJK-CKPIZJOLSA-N
Standard InCHI:	InChI=1S/C36H58O9/c1-19(9-13-25(38)33(4,5)43)20-15-16-34(6)24-12-10-21-22(36(24,8)26(39)17-35(20,34)7)11-14-27(32(21,2)3)45-31-30(42)29(41)28(40)23(18-37)44-31/h10,19-20,22-24,27-31,37,40-43H,9,11-18H2,1-8H3/t19-,20-,22-,23-,24+,27+,28-,29+,30-,31+,34+,35-,36+/m1/s1
SMILES:	C[C@H](CCC(=O)C(C)(C)O)[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451089
PubChem CID:	10985073
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
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11858752]
NPO33132	bryonia dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[521743]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[521743]
NPT2	Others	Unspecified		Inhibition	=	29.2	%	PMID[521743]
NPT2	Others	Unspecified		Inhibition	=	71.4	%	PMID[521743]
NPT2	Others	Unspecified		Inhibition	=	97.6	%	PMID[521743]

☑ 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 NPC130427 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	238
0.1-0.2	1491
0.2-0.3	4884
0.3-0.4	10507
0.4-0.5	10513
0.5-0.6	6072
0.6-0.7	5087
0.7-0.8	3068
0.8-0.85	663
0.85-0.9	141
0.9-0.95	28
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC474557
0.9806	High Similarity	NPC475317
0.9806	High Similarity	NPC154856
0.9806	High Similarity	NPC52241
0.9619	High Similarity	NPC474265
0.9619	High Similarity	NPC210420
0.9439	High Similarity	NPC473882
0.9364	High Similarity	NPC471406
0.9352	High Similarity	NPC279638
0.9259	High Similarity	NPC74727
0.9238	High Similarity	NPC295389
0.9167	High Similarity	NPC260665
0.9159	High Similarity	NPC250481
0.9159	High Similarity	NPC285410
0.9159	High Similarity	NPC263827
0.9151	High Similarity	NPC246205
0.9065	High Similarity	NPC129340
0.9048	High Similarity	NPC210178
0.9048	High Similarity	NPC63023
0.9048	High Similarity	NPC95243
0.9018	High Similarity	NPC472257
0.9009	High Similarity	NPC475632
0.9009	High Similarity	NPC86020
0.9009	High Similarity	NPC45475
0.8991	High Similarity	NPC477944
0.8991	High Similarity	NPC251309
0.8981	High Similarity	NPC269466
0.8972	High Similarity	NPC477069
0.8972	High Similarity	NPC265655
0.8972	High Similarity	NPC118225
0.8972	High Similarity	NPC477070
0.8952	High Similarity	NPC100955
0.8952	High Similarity	NPC121566
0.8938	High Similarity	NPC476545
0.8938	High Similarity	NPC476544
0.8938	High Similarity	NPC476543
0.8909	High Similarity	NPC165439
0.8899	High Similarity	NPC233003
0.8889	High Similarity	NPC101450
0.8879	High Similarity	NPC195708
0.887	High Similarity	NPC475194
0.8868	High Similarity	NPC162033
0.885	High Similarity	NPC475187
0.885	High Similarity	NPC472075
0.885	High Similarity	NPC472076
0.8829	High Similarity	NPC244127
0.8807	High Similarity	NPC292196
0.8807	High Similarity	NPC477073
0.8803	High Similarity	NPC293623
0.8803	High Similarity	NPC69273
0.8803	High Similarity	NPC168899
0.8796	High Similarity	NPC8431
0.8783	High Similarity	NPC476542
0.8774	High Similarity	NPC223741
0.8774	High Similarity	NPC470885
0.8774	High Similarity	NPC221562
0.8774	High Similarity	NPC187400
0.8762	High Similarity	NPC136816
0.8761	High Similarity	NPC477071
0.8761	High Similarity	NPC161738
0.8739	High Similarity	NPC220293
0.8739	High Similarity	NPC477580
0.8739	High Similarity	NPC116024
0.8738	High Similarity	NPC473890
0.8738	High Similarity	NPC243728
0.8729	High Similarity	NPC471407
0.8727	High Similarity	NPC46388
0.8727	High Similarity	NPC37739
0.8716	High Similarity	NPC114961
0.8716	High Similarity	NPC27551
0.8716	High Similarity	NPC274507
0.8704	High Similarity	NPC258323
0.8696	High Similarity	NPC156789
0.8696	High Similarity	NPC28532
0.8696	High Similarity	NPC475431
0.8692	High Similarity	NPC473199
0.8692	High Similarity	NPC309448
0.8684	High Similarity	NPC129393
0.8673	High Similarity	NPC239293
0.8667	High Similarity	NPC88000
0.8667	High Similarity	NPC4831
0.8667	High Similarity	NPC160734
0.8667	High Similarity	NPC129372
0.8667	High Similarity	NPC472023
0.8667	High Similarity	NPC47566
0.8667	High Similarity	NPC309425
0.8655	High Similarity	NPC241008
0.8654	High Similarity	NPC158088
0.8649	High Similarity	NPC189884
0.8649	High Similarity	NPC62696
0.8649	High Similarity	NPC138334
0.8649	High Similarity	NPC271138
0.8649	High Similarity	NPC73455
0.8649	High Similarity	NPC204458
0.8649	High Similarity	NPC47063
0.8649	High Similarity	NPC200944
0.8649	High Similarity	NPC178981
0.8649	High Similarity	NPC269315
0.8649	High Similarity	NPC477074
0.8649	High Similarity	NPC293038
0.8636	High Similarity	NPC108748
0.8636	High Similarity	NPC211798
0.8636	High Similarity	NPC297208
0.8636	High Similarity	NPC274833
0.8636	High Similarity	NPC235841
0.8636	High Similarity	NPC30397
0.8636	High Similarity	NPC473481
0.8636	High Similarity	NPC191763
0.8624	High Similarity	NPC218853
0.8624	High Similarity	NPC306746
0.8624	High Similarity	NPC137917
0.8624	High Similarity	NPC204407
0.8624	High Similarity	NPC167383
0.8624	High Similarity	NPC237503
0.8624	High Similarity	NPC57362
0.8621	High Similarity	NPC160084
0.8621	High Similarity	NPC472077
0.8621	High Similarity	NPC472078
0.8611	High Similarity	NPC293512
0.8611	High Similarity	NPC190395
0.8611	High Similarity	NPC226642
0.8611	High Similarity	NPC33053
0.8609	High Similarity	NPC202051
0.8609	High Similarity	NPC249553
0.8609	High Similarity	NPC475182
0.8609	High Similarity	NPC42675
0.8609	High Similarity	NPC182900
0.8609	High Similarity	NPC476672
0.8609	High Similarity	NPC476675
0.8598	High Similarity	NPC93352
0.8598	High Similarity	NPC75608
0.8596	High Similarity	NPC190939
0.8596	High Similarity	NPC197003
0.8585	High Similarity	NPC272015
0.8585	High Similarity	NPC154452
0.8585	High Similarity	NPC94919
0.8584	High Similarity	NPC309433
0.8583	High Similarity	NPC471855
0.8583	High Similarity	NPC473519
0.8583	High Similarity	NPC473805
0.8571	High Similarity	NPC7341
0.8571	High Similarity	NPC167974
0.8571	High Similarity	NPC102088
0.8571	High Similarity	NPC473200
0.8571	High Similarity	NPC282669
0.8559	High Similarity	NPC471967
0.8559	High Similarity	NPC256798
0.8559	High Similarity	NPC472719
0.8559	High Similarity	NPC477253
0.8559	High Similarity	NPC128925
0.8559	High Similarity	NPC116794
0.8559	High Similarity	NPC207845
0.8547	High Similarity	NPC473474
0.8547	High Similarity	NPC476674
0.8547	High Similarity	NPC130229
0.8545	High Similarity	NPC270667
0.8545	High Similarity	NPC75747
0.8545	High Similarity	NPC29069
0.8545	High Similarity	NPC476885
0.8545	High Similarity	NPC269095
0.8545	High Similarity	NPC110139
0.8545	High Similarity	NPC136877
0.8545	High Similarity	NPC56713
0.8545	High Similarity	NPC78046
0.8545	High Similarity	NPC68419
0.8545	High Similarity	NPC174679
0.8545	High Similarity	NPC279554
0.8545	High Similarity	NPC474589
0.8545	High Similarity	NPC476882
0.8545	High Similarity	NPC220984
0.8545	High Similarity	NPC476884
0.8545	High Similarity	NPC476887
0.8545	High Similarity	NPC476881
0.8545	High Similarity	NPC59804
0.8545	High Similarity	NPC108709
0.8545	High Similarity	NPC102914
0.8545	High Similarity	NPC7870
0.8545	High Similarity	NPC476880
0.8545	High Similarity	NPC164194
0.8545	High Similarity	NPC90856
0.8545	High Similarity	NPC199457
0.8545	High Similarity	NPC127056
0.8545	High Similarity	NPC476886
0.8545	High Similarity	NPC470065
0.8545	High Similarity	NPC475296
0.8545	High Similarity	NPC476883
0.8534	High Similarity	NPC94072
0.8534	High Similarity	NPC305771
0.8534	High Similarity	NPC169816
0.8534	High Similarity	NPC15918
0.8532	High Similarity	NPC177246
0.8532	High Similarity	NPC295980
0.8532	High Similarity	NPC472988
0.8532	High Similarity	NPC38217
0.8532	High Similarity	NPC28198
0.8532	High Similarity	NPC476123
0.8532	High Similarity	NPC284807
0.8532	High Similarity	NPC88744
0.8522	High Similarity	NPC308459
0.8519	High Similarity	NPC473476

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 NPC130427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1735
0.2-0.3	3994
0.3-0.4	2076
0.4-0.5	604
0.5-0.6	236
0.6-0.7	174
0.7-0.8	119
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8785	High Similarity	NPD6412	Phase 2
0.8288	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD6370	Approved
0.8182	Intermediate Similarity	NPD7736	Approved
0.8151	Intermediate Similarity	NPD8328	Phase 3
0.8103	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD8293	Discontinued
0.8051	Intermediate Similarity	NPD6059	Approved
0.8051	Intermediate Similarity	NPD6054	Approved
0.8017	Intermediate Similarity	NPD7507	Approved
0.8	Intermediate Similarity	NPD8133	Approved
0.7913	Intermediate Similarity	NPD6882	Approved
0.7913	Intermediate Similarity	NPD8297	Approved
0.7876	Intermediate Similarity	NPD6686	Approved
0.7833	Intermediate Similarity	NPD6015	Approved
0.7833	Intermediate Similarity	NPD8033	Approved
0.7833	Intermediate Similarity	NPD6016	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7797	Intermediate Similarity	NPD6009	Approved
0.7787	Intermediate Similarity	NPD7492	Approved
0.7769	Intermediate Similarity	NPD5988	Approved
0.775	Intermediate Similarity	NPD8294	Approved
0.775	Intermediate Similarity	NPD8377	Approved
0.775	Intermediate Similarity	NPD6319	Approved
0.7731	Intermediate Similarity	NPD7327	Approved
0.7731	Intermediate Similarity	NPD7328	Approved
0.7724	Intermediate Similarity	NPD6616	Approved
0.7699	Intermediate Similarity	NPD6675	Approved
0.7699	Intermediate Similarity	NPD6402	Approved
0.7699	Intermediate Similarity	NPD7128	Approved
0.7699	Intermediate Similarity	NPD5739	Approved
0.7692	Intermediate Similarity	NPD4632	Approved
0.7686	Intermediate Similarity	NPD8296	Approved
0.7686	Intermediate Similarity	NPD8380	Approved
0.7686	Intermediate Similarity	NPD8379	Approved
0.7686	Intermediate Similarity	NPD8335	Approved
0.7686	Intermediate Similarity	NPD8378	Approved
0.7667	Intermediate Similarity	NPD7516	Approved
0.7664	Intermediate Similarity	NPD6399	Phase 3
0.7661	Intermediate Similarity	NPD7078	Approved
0.7652	Intermediate Similarity	NPD6373	Approved
0.7652	Intermediate Similarity	NPD6372	Approved
0.7573	Intermediate Similarity	NPD4786	Approved
0.7565	Intermediate Similarity	NPD7320	Approved
0.7565	Intermediate Similarity	NPD6899	Approved
0.7565	Intermediate Similarity	NPD6881	Approved
0.7545	Intermediate Similarity	NPD6083	Phase 2
0.7545	Intermediate Similarity	NPD4755	Approved
0.7545	Intermediate Similarity	NPD6084	Phase 2
0.7541	Intermediate Similarity	NPD7503	Approved
0.7521	Intermediate Similarity	NPD8130	Phase 1
0.7521	Intermediate Similarity	NPD6649	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.7478	Intermediate Similarity	NPD5701	Approved
0.7478	Intermediate Similarity	NPD5697	Approved
0.746	Intermediate Similarity	NPD6033	Approved
0.7456	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6883	Approved
0.7436	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD4634	Approved
0.7436	Intermediate Similarity	NPD7102	Approved
0.7419	Intermediate Similarity	NPD6067	Discontinued
0.7411	Intermediate Similarity	NPD5285	Approved
0.7411	Intermediate Similarity	NPD5286	Approved
0.7411	Intermediate Similarity	NPD4700	Approved
0.7411	Intermediate Similarity	NPD4696	Approved
0.7383	Intermediate Similarity	NPD4753	Phase 2
0.7379	Intermediate Similarity	NPD3667	Approved
0.7373	Intermediate Similarity	NPD6869	Approved
0.7373	Intermediate Similarity	NPD6847	Approved
0.7373	Intermediate Similarity	NPD6617	Approved
0.7355	Intermediate Similarity	NPD7115	Discovery
0.735	Intermediate Similarity	NPD6013	Approved
0.735	Intermediate Similarity	NPD6012	Approved
0.735	Intermediate Similarity	NPD6014	Approved
0.7281	Intermediate Similarity	NPD5225	Approved
0.7281	Intermediate Similarity	NPD5211	Phase 2
0.7281	Intermediate Similarity	NPD4633	Approved
0.7281	Intermediate Similarity	NPD5224	Approved
0.7281	Intermediate Similarity	NPD5226	Approved
0.728	Intermediate Similarity	NPD7604	Phase 2
0.7265	Intermediate Similarity	NPD6011	Approved
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.7258	Intermediate Similarity	NPD5983	Phase 2
0.7258	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8515	Approved
0.7241	Intermediate Similarity	NPD4768	Approved
0.7241	Intermediate Similarity	NPD4767	Approved
0.7227	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5328	Approved
0.7217	Intermediate Similarity	NPD5175	Approved
0.7217	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7193	Intermediate Similarity	NPD5223	Approved
0.7182	Intermediate Similarity	NPD4202	Approved
0.7168	Intermediate Similarity	NPD5696	Approved
0.7165	Intermediate Similarity	NPD6336	Discontinued
0.7155	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6672	Approved
0.713	Intermediate Similarity	NPD5737	Approved
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4729	Approved
0.7119	Intermediate Similarity	NPD4730	Approved
0.7117	Intermediate Similarity	NPD7748	Approved
0.7103	Intermediate Similarity	NPD3618	Phase 1
0.7094	Intermediate Similarity	NPD6008	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7091	Intermediate Similarity	NPD6079	Approved
0.708	Intermediate Similarity	NPD7902	Approved
0.708	Intermediate Similarity	NPD5173	Approved
0.7077	Intermediate Similarity	NPD5956	Approved
0.7069	Intermediate Similarity	NPD4754	Approved
0.7054	Intermediate Similarity	NPD5210	Approved
0.7054	Intermediate Similarity	NPD4629	Approved
0.7018	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD5249	Phase 3
0.7	Intermediate Similarity	NPD5251	Approved
0.7	Intermediate Similarity	NPD5247	Approved
0.6992	Remote Similarity	NPD6274	Approved
0.6975	Remote Similarity	NPD5128	Approved
0.696	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD7640	Approved
0.6957	Remote Similarity	NPD7639	Approved
0.6944	Remote Similarity	NPD5279	Phase 3
0.6944	Remote Similarity	NPD6098	Approved
0.6937	Remote Similarity	NPD7515	Phase 2
0.6917	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3665	Phase 1
0.6916	Remote Similarity	NPD4197	Approved
0.6916	Remote Similarity	NPD3133	Approved
0.6916	Remote Similarity	NPD3668	Phase 3
0.6916	Remote Similarity	NPD3666	Approved
0.6909	Remote Similarity	NPD6673	Approved
0.6909	Remote Similarity	NPD6080	Approved
0.6909	Remote Similarity	NPD6904	Approved
0.6881	Remote Similarity	NPD7524	Approved
0.688	Remote Similarity	NPD6335	Approved
0.6875	Remote Similarity	NPD8171	Discontinued
0.6857	Remote Similarity	NPD7525	Registered
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6908	Approved
0.685	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD8449	Approved
0.6818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7900	Approved
0.6803	Remote Similarity	NPD5215	Approved
0.6803	Remote Similarity	NPD5216	Approved
0.6803	Remote Similarity	NPD5217	Approved
0.68	Remote Similarity	NPD6317	Approved
0.6791	Remote Similarity	NPD8450	Suspended
0.6789	Remote Similarity	NPD6684	Approved
0.6789	Remote Similarity	NPD6409	Approved
0.6789	Remote Similarity	NPD7334	Approved
0.6789	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD7521	Approved
0.6789	Remote Similarity	NPD7146	Approved
0.6759	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6314	Approved
0.6746	Remote Similarity	NPD6313	Approved
0.6729	Remote Similarity	NPD4221	Approved
0.6729	Remote Similarity	NPD4223	Phase 3
0.6721	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5135	Approved
0.6721	Remote Similarity	NPD5169	Approved
0.672	Remote Similarity	NPD6868	Approved
0.6699	Remote Similarity	NPD7339	Approved
0.6699	Remote Similarity	NPD6942	Approved
0.6693	Remote Similarity	NPD4522	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6637	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD6050	Approved
0.6636	Remote Similarity	NPD5280	Approved
0.6636	Remote Similarity	NPD4694	Approved
0.6636	Remote Similarity	NPD5690	Phase 2
0.6613	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8074	Phase 3
0.6589	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6921	Approved
0.6577	Remote Similarity	NPD7750	Discontinued
0.6557	Remote Similarity	NPD5168	Approved
0.6549	Remote Similarity	NPD5692	Phase 3
0.6549	Remote Similarity	NPD46	Approved
0.6549	Remote Similarity	NPD6698	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