NPASS Compound

Structure

NPC154856 OpenBabel07101718302D 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 2 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 1 6 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:	636.42
Volume:	662.269
LogP:	3.965
LogD:	3.74
LogS:	-4.077
# Rotatable Bonds:	8
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	5.465
Fsp3:	0.917
Lipinski Rule-of-5:	Rejected
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:	-4.998
MDCK Permeability:	1.1767002433771268e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.763

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	86.19691467285156%
Volume Distribution (VD):	0.725
Pgp-substrate:	5.411576271057129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	2.605
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.281
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC154856

Natural Product ID:	NPC154856
*Common Name:**	Cabenoside D
IUPAC Name:	(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-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:	cabenoside D
Standard InCHIKey:	XMWIWVZEGGOMAU-CDPRDXQRSA-N
Standard InCHI:	InChI=1S/C36H60O9/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/h10,19-20,22-25,27-31,37-38,40-43H,9,11-18H2,1-8H3/t19-,20-,22-,23-,24+,25-,27+,28-,29+,30-,31+,34+,35-,36+/m1/s1
SMILES:	C[C@H](CC[C@H](C(C)(C)O)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:	CHEMBL510167
PubChem CID:	44584114
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	7

Activity Type	# Activity
Cell Line	1
Organism	2
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[538453]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[538453]
NPT2	Others	Unspecified		Inhibition	=	26.1	%	PMID[538453]
NPT2	Others	Unspecified		Inhibition	=	69.3	%	PMID[538453]
NPT2	Others	Unspecified		Inhibition	=	94.1	%	PMID[538453]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.6	mg	PMID[538453]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	66.0	%	PMID[538453]

☑ 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 NPC154856 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	231
0.1-0.2	1451
0.2-0.3	4738
0.3-0.4	10427
0.4-0.5	10557
0.5-0.6	6057
0.6-0.7	4962
0.7-0.8	3311
0.8-0.85	752
0.85-0.9	163
0.9-0.95	41
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52241
1.0	High Similarity	NPC475317
0.9806	High Similarity	NPC474265
0.9806	High Similarity	NPC210420
0.9806	High Similarity	NPC130427
0.9619	High Similarity	NPC474557
0.9619	High Similarity	NPC473882
0.9528	High Similarity	NPC279638
0.9434	High Similarity	NPC74727
0.9417	High Similarity	NPC295389
0.934	High Similarity	NPC260665
0.9333	High Similarity	NPC263827
0.9333	High Similarity	NPC250481
0.9333	High Similarity	NPC285410
0.9327	High Similarity	NPC246205
0.9238	High Similarity	NPC129340
0.9223	High Similarity	NPC63023
0.9223	High Similarity	NPC210178
0.9223	High Similarity	NPC95243
0.9182	High Similarity	NPC471406
0.9174	High Similarity	NPC45475
0.9174	High Similarity	NPC475632
0.9174	High Similarity	NPC86020
0.9159	High Similarity	NPC251309
0.9159	High Similarity	NPC477944
0.9151	High Similarity	NPC269466
0.9143	High Similarity	NPC118225
0.9143	High Similarity	NPC477069
0.9143	High Similarity	NPC477070
0.9143	High Similarity	NPC265655
0.9126	High Similarity	NPC100955
0.9126	High Similarity	NPC121566
0.9074	High Similarity	NPC165439
0.9065	High Similarity	NPC233003
0.9057	High Similarity	NPC101450
0.9048	High Similarity	NPC195708
0.9038	High Similarity	NPC162033
0.9009	High Similarity	NPC475187
0.8991	High Similarity	NPC244127
0.8972	High Similarity	NPC477073
0.8972	High Similarity	NPC292196
0.8962	High Similarity	NPC8431
0.8942	High Similarity	NPC187400
0.8942	High Similarity	NPC221562
0.8942	High Similarity	NPC470885
0.8942	High Similarity	NPC223741
0.8932	High Similarity	NPC136816
0.8919	High Similarity	NPC477071
0.8919	High Similarity	NPC161738
0.8911	High Similarity	NPC243728
0.8911	High Similarity	NPC473890
0.8899	High Similarity	NPC477580
0.8899	High Similarity	NPC220293
0.8899	High Similarity	NPC116024
0.8889	High Similarity	NPC46388
0.8889	High Similarity	NPC37739
0.8879	High Similarity	NPC274507
0.8879	High Similarity	NPC114961
0.8879	High Similarity	NPC27551
0.8868	High Similarity	NPC258323
0.8857	High Similarity	NPC473199
0.8857	High Similarity	NPC309448
0.885	High Similarity	NPC475431
0.885	High Similarity	NPC28532
0.885	High Similarity	NPC156789
0.8839	High Similarity	NPC472257
0.8839	High Similarity	NPC129393
0.8835	High Similarity	NPC309425
0.8835	High Similarity	NPC88000
0.8835	High Similarity	NPC129372
0.8835	High Similarity	NPC472023
0.8835	High Similarity	NPC47566
0.8835	High Similarity	NPC160734
0.8835	High Similarity	NPC4831
0.8829	High Similarity	NPC239293
0.8824	High Similarity	NPC158088
0.8807	High Similarity	NPC47063
0.8807	High Similarity	NPC62696
0.8807	High Similarity	NPC73455
0.8807	High Similarity	NPC271138
0.8807	High Similarity	NPC293038
0.8807	High Similarity	NPC200944
0.8807	High Similarity	NPC189884
0.8807	High Similarity	NPC138334
0.8807	High Similarity	NPC178981
0.8807	High Similarity	NPC269315
0.8807	High Similarity	NPC204458
0.8807	High Similarity	NPC477074
0.8796	High Similarity	NPC191763
0.8796	High Similarity	NPC473481
0.8796	High Similarity	NPC235841
0.8796	High Similarity	NPC297208
0.8796	High Similarity	NPC274833
0.8796	High Similarity	NPC108748
0.8796	High Similarity	NPC30397
0.8796	High Similarity	NPC211798
0.8785	High Similarity	NPC137917
0.8785	High Similarity	NPC306746
0.8785	High Similarity	NPC218853
0.8785	High Similarity	NPC167383
0.8785	High Similarity	NPC204407
0.8785	High Similarity	NPC57362
0.8785	High Similarity	NPC237503
0.8774	High Similarity	NPC226642
0.8774	High Similarity	NPC190395
0.8774	High Similarity	NPC33053
0.8774	High Similarity	NPC293512
0.8772	High Similarity	NPC160084
0.8762	High Similarity	NPC75608
0.8762	High Similarity	NPC93352
0.8761	High Similarity	NPC476545
0.8761	High Similarity	NPC476675
0.8761	High Similarity	NPC476543
0.8761	High Similarity	NPC182900
0.8761	High Similarity	NPC476672
0.8761	High Similarity	NPC476544
0.8761	High Similarity	NPC202051
0.8761	High Similarity	NPC249553
0.8761	High Similarity	NPC475182
0.875	High Similarity	NPC94919
0.875	High Similarity	NPC272015
0.875	High Similarity	NPC190939
0.875	High Similarity	NPC154452
0.875	High Similarity	NPC197003
0.8738	High Similarity	NPC473200
0.8738	High Similarity	NPC7341
0.8738	High Similarity	NPC167974
0.8738	High Similarity	NPC282669
0.8727	High Similarity	NPC102088
0.8716	High Similarity	NPC207845
0.8716	High Similarity	NPC128925
0.8716	High Similarity	NPC116794
0.8716	High Similarity	NPC471967
0.8716	High Similarity	NPC256798
0.8716	High Similarity	NPC472719
0.8716	High Similarity	NPC477253
0.8704	High Similarity	NPC476887
0.8704	High Similarity	NPC7870
0.8704	High Similarity	NPC199457
0.8704	High Similarity	NPC269095
0.8704	High Similarity	NPC127056
0.8704	High Similarity	NPC59804
0.8704	High Similarity	NPC476886
0.8704	High Similarity	NPC475296
0.8704	High Similarity	NPC174679
0.8704	High Similarity	NPC108709
0.8704	High Similarity	NPC476885
0.8704	High Similarity	NPC75747
0.8704	High Similarity	NPC270667
0.8704	High Similarity	NPC279554
0.8704	High Similarity	NPC476880
0.8704	High Similarity	NPC476884
0.8704	High Similarity	NPC136877
0.8704	High Similarity	NPC56713
0.8704	High Similarity	NPC29069
0.8704	High Similarity	NPC78046
0.8704	High Similarity	NPC220984
0.8704	High Similarity	NPC476883
0.8704	High Similarity	NPC476882
0.8704	High Similarity	NPC470065
0.8704	High Similarity	NPC474589
0.8704	High Similarity	NPC102914
0.8704	High Similarity	NPC476881
0.8704	High Similarity	NPC68419
0.8704	High Similarity	NPC110139
0.8704	High Similarity	NPC164194
0.8704	High Similarity	NPC90856
0.8696	High Similarity	NPC475194
0.8696	High Similarity	NPC476674
0.8696	High Similarity	NPC473474
0.8692	High Similarity	NPC38217
0.8692	High Similarity	NPC88744
0.8692	High Similarity	NPC284807
0.8692	High Similarity	NPC177246
0.8692	High Similarity	NPC476123
0.8692	High Similarity	NPC295980
0.8692	High Similarity	NPC472988
0.8692	High Similarity	NPC28198
0.8684	High Similarity	NPC15918
0.8684	High Similarity	NPC305771
0.8684	High Similarity	NPC94072
0.8684	High Similarity	NPC169816
0.8679	High Similarity	NPC473923
0.8679	High Similarity	NPC474569
0.8679	High Similarity	NPC472900
0.8679	High Similarity	NPC473476
0.8679	High Similarity	NPC242748
0.8679	High Similarity	NPC472898
0.8679	High Similarity	NPC472899
0.8673	High Similarity	NPC472075
0.8673	High Similarity	NPC308459
0.8673	High Similarity	NPC472076
0.8667	High Similarity	NPC157659
0.8667	High Similarity	NPC245280
0.8667	High Similarity	NPC473020
0.8667	High Similarity	NPC189852
0.8667	High Similarity	NPC16520
0.8667	High Similarity	NPC213190
0.8667	High Similarity	NPC114874
0.8667	High Similarity	NPC286969

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 NPC154856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1686
0.2-0.3	3988
0.3-0.4	2123
0.4-0.5	614
0.5-0.6	229
0.6-0.7	202
0.7-0.8	104
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8952	High Similarity	NPD6412	Phase 2
0.844	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD7507	Approved
0.8142	Intermediate Similarity	NPD8133	Approved
0.8051	Intermediate Similarity	NPD6370	Approved
0.8018	Intermediate Similarity	NPD6686	Approved
0.8017	Intermediate Similarity	NPD7736	Approved
0.7983	Intermediate Similarity	NPD8328	Phase 3
0.7966	Intermediate Similarity	NPD8033	Approved
0.7951	Intermediate Similarity	NPD7319	Approved
0.7934	Intermediate Similarity	NPD8293	Discontinued
0.7931	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD8377	Approved
0.7881	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD6054	Approved
0.7881	Intermediate Similarity	NPD6059	Approved
0.7863	Intermediate Similarity	NPD7327	Approved
0.7863	Intermediate Similarity	NPD7328	Approved
0.7815	Intermediate Similarity	NPD8380	Approved
0.7815	Intermediate Similarity	NPD8379	Approved
0.7815	Intermediate Similarity	NPD8296	Approved
0.7815	Intermediate Similarity	NPD8378	Approved
0.7815	Intermediate Similarity	NPD8335	Approved
0.781	Intermediate Similarity	NPD6399	Phase 3
0.7797	Intermediate Similarity	NPD7516	Approved
0.7739	Intermediate Similarity	NPD6882	Approved
0.7739	Intermediate Similarity	NPD8297	Approved
0.7723	Intermediate Similarity	NPD4786	Approved
0.7667	Intermediate Similarity	NPD7503	Approved
0.7667	Intermediate Similarity	NPD6016	Approved
0.7667	Intermediate Similarity	NPD6015	Approved
0.7627	Intermediate Similarity	NPD6009	Approved
0.7623	Intermediate Similarity	NPD7492	Approved
0.7603	Intermediate Similarity	NPD5988	Approved
0.7589	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6319	Approved
0.7561	Intermediate Similarity	NPD6616	Approved
0.7541	Intermediate Similarity	NPD6067	Discontinued
0.7525	Intermediate Similarity	NPD3667	Approved
0.7522	Intermediate Similarity	NPD7128	Approved
0.7522	Intermediate Similarity	NPD6402	Approved
0.7522	Intermediate Similarity	NPD5739	Approved
0.7522	Intermediate Similarity	NPD6675	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.7479	Intermediate Similarity	NPD7115	Discovery
0.7478	Intermediate Similarity	NPD6373	Approved
0.7478	Intermediate Similarity	NPD6372	Approved
0.7391	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD6881	Approved
0.7391	Intermediate Similarity	NPD7320	Approved
0.7377	Intermediate Similarity	NPD8513	Phase 3
0.7377	Intermediate Similarity	NPD8516	Approved
0.7377	Intermediate Similarity	NPD8517	Approved
0.7377	Intermediate Similarity	NPD8515	Approved
0.7364	Intermediate Similarity	NPD6084	Phase 2
0.7364	Intermediate Similarity	NPD6083	Phase 2
0.7364	Intermediate Similarity	NPD4755	Approved
0.7358	Intermediate Similarity	NPD5328	Approved
0.735	Intermediate Similarity	NPD8130	Phase 1
0.735	Intermediate Similarity	NPD6650	Approved
0.735	Intermediate Similarity	NPD6649	Approved
0.7315	Intermediate Similarity	NPD4202	Approved
0.7304	Intermediate Similarity	NPD5701	Approved
0.7304	Intermediate Similarity	NPD5697	Approved
0.7302	Intermediate Similarity	NPD6033	Approved
0.7265	Intermediate Similarity	NPD7290	Approved
0.7265	Intermediate Similarity	NPD6883	Approved
0.7265	Intermediate Similarity	NPD7102	Approved
0.7265	Intermediate Similarity	NPD4634	Approved
0.7248	Intermediate Similarity	NPD7748	Approved
0.7238	Intermediate Similarity	NPD3618	Phase 1
0.7232	Intermediate Similarity	NPD4696	Approved
0.7232	Intermediate Similarity	NPD5285	Approved
0.7232	Intermediate Similarity	NPD5286	Approved
0.7232	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD6079	Approved
0.7222	Intermediate Similarity	NPD8035	Phase 2
0.7217	Intermediate Similarity	NPD6008	Approved
0.7207	Intermediate Similarity	NPD7902	Approved
0.7203	Intermediate Similarity	NPD6847	Approved
0.7203	Intermediate Similarity	NPD6617	Approved
0.7203	Intermediate Similarity	NPD6869	Approved
0.7196	Intermediate Similarity	NPD4753	Phase 2
0.7179	Intermediate Similarity	NPD6014	Approved
0.7179	Intermediate Similarity	NPD6012	Approved
0.7179	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.712	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD5224	Approved
0.7105	Intermediate Similarity	NPD5211	Phase 2
0.7105	Intermediate Similarity	NPD5225	Approved
0.7105	Intermediate Similarity	NPD5226	Approved
0.7105	Intermediate Similarity	NPD4633	Approved
0.7097	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6011	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.7069	Intermediate Similarity	NPD4767	Approved
0.7069	Intermediate Similarity	NPD4768	Approved
0.7064	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3133	Approved
0.7048	Intermediate Similarity	NPD3666	Approved
0.7048	Intermediate Similarity	NPD3665	Phase 1
0.7048	Intermediate Similarity	NPD3668	Phase 3
0.7043	Intermediate Similarity	NPD5175	Approved
0.7043	Intermediate Similarity	NPD5174	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5695	Phase 3
0.7018	Intermediate Similarity	NPD5223	Approved
0.7009	Intermediate Similarity	NPD7524	Approved
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD8171	Discontinued
0.6991	Remote Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD7525	Registered
0.6983	Remote Similarity	NPD5141	Approved
0.6981	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5222	Approved
0.6964	Remote Similarity	NPD5221	Approved
0.6964	Remote Similarity	NPD4697	Phase 3
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4730	Approved
0.6949	Remote Similarity	NPD4729	Approved
0.6947	Remote Similarity	NPD8449	Approved
0.6944	Remote Similarity	NPD6672	Approved
0.6944	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5737	Approved
0.6937	Remote Similarity	NPD7900	Approved
0.6937	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5956	Approved
0.6916	Remote Similarity	NPD7334	Approved
0.6916	Remote Similarity	NPD6409	Approved
0.6916	Remote Similarity	NPD6684	Approved
0.6916	Remote Similarity	NPD7146	Approved
0.6916	Remote Similarity	NPD7521	Approved
0.6916	Remote Similarity	NPD5330	Approved
0.6903	Remote Similarity	NPD5173	Approved
0.6897	Remote Similarity	NPD4754	Approved
0.6894	Remote Similarity	NPD8450	Suspended
0.6887	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.6857	Remote Similarity	NPD4223	Phase 3
0.6857	Remote Similarity	NPD4221	Approved
0.6833	Remote Similarity	NPD5249	Phase 3
0.6833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5251	Approved
0.6833	Remote Similarity	NPD5247	Approved
0.6833	Remote Similarity	NPD5250	Approved
0.6833	Remote Similarity	NPD5248	Approved
0.6832	Remote Similarity	NPD7339	Approved
0.6832	Remote Similarity	NPD6942	Approved
0.6829	Remote Similarity	NPD6274	Approved
0.6822	Remote Similarity	NPD5329	Approved
0.6807	Remote Similarity	NPD5128	Approved
0.68	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD7100	Approved
0.6792	Remote Similarity	NPD6695	Phase 3
0.6789	Remote Similarity	NPD6903	Approved
0.6759	Remote Similarity	NPD6098	Approved
0.6759	Remote Similarity	NPD5279	Phase 3
0.6729	Remote Similarity	NPD4197	Approved
0.6727	Remote Similarity	NPD6080	Approved
0.6727	Remote Similarity	NPD6904	Approved
0.6727	Remote Similarity	NPD6673	Approved
0.6726	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6053	Discontinued
0.672	Remote Similarity	NPD6335	Approved
0.6697	Remote Similarity	NPD7750	Discontinued
0.6693	Remote Similarity	NPD6909	Approved
0.6693	Remote Similarity	NPD6908	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6641	Remote Similarity	NPD8336	Approved
0.6641	Remote Similarity	NPD8337	Approved
0.664	Remote Similarity	NPD6317	Approved
0.6639	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5217	Approved
0.6639	Remote Similarity	NPD5215	Approved
0.6636	Remote Similarity	NPD4788	Approved
0.6607	Remote Similarity	NPD6411	Approved
0.6607	Remote Similarity	NPD7637	Suspended
0.6607	Remote Similarity	NPD5281	Approved
0.6607	Remote Similarity	NPD5284	Approved
0.6606	Remote Similarity	NPD4693	Phase 3
0.6606	Remote Similarity	NPD4138	Approved
0.6606	Remote Similarity	NPD4688	Approved
0.6606	Remote Similarity	NPD4689	Approved
0.6606	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5205	Approved
0.6606	Remote Similarity	NPD4690	Approved
0.6602	Remote Similarity	NPD6933	Approved
0.6602	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6314	Approved
0.6587	Remote Similarity	NPD6313	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