NPASS Compound

Structure

NPC471293 OpenBabel07101718292D 35 39 0 0 1 0 0 0 0 0999 V2000 -4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8023 -2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2091 -1.4271 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 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 -0.1303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1100 -0.5371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9941 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2146 -1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9191 0.0507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4941 1.8184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4055 -2.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 17 16 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 30 1 0 0 0 0 21 24 1 1 0 0 0 21 35 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 27 1 0 0 0 0 24 32 1 6 0 0 0 25 33 2 0 0 0 0 25 35 1 0 0 0 0 27 34 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	5.255
LogD:	4.373
LogS:	-4.151
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	5.035
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788
MDCK Permeability:	1.7645308616920374e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.099
30% Bioavailability (F30%):	0.381

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.431
Plasma Protein Binding (PPB):	90.538818359375%
Volume Distribution (VD):	1.329
Pgp-substrate:	6.081355571746826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.609

ADMET: Excretion

Clearance (CL):	7.342
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.235
Carcinogencity:	0.068
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC471293

Natural Product ID:	NPC471293
*Common Name:**	Cochinchinoid K
IUPAC Name:	(3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-3-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxolan-2-one
Synonyms:
Standard InCHIKey:	QDVOKJAQMSSOJK-FQARURFKSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-26(2)22-9-8-20-19(28(22,5)13-12-23(26)31)11-15-29(6)18(10-14-30(20,29)7)17-16-21(35-25(17)33)24(32)27(3,4)34/h8,17-19,21-24,31-32,34H,9-16H2,1-7H3/t17-,18-,19-,21+,22-,23-,24-,28+,29-,30+/m0/s1
SMILES:	CC1(C(CCC2(C1CC=C3C2CCC4(C3(CCC4C5CC(OC5=O)C(C(C)(C)O)O)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409065
PubChem CID:	71745149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	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
IC50	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	820.0	nM	PMID[547463]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	3200.0	nM	PMID[547463]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	>	60.0	%	PMID[547463]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	>	60.0	%	PMID[547463]

☑ 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 NPC471293 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	207
0.1-0.2	1178
0.2-0.3	4538
0.3-0.4	10205
0.4-0.5	11237
0.5-0.6	5503
0.6-0.7	5766
0.7-0.8	3778
0.8-0.85	235
0.85-0.9	46
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC59530
0.901	High Similarity	NPC255309
0.8958	High Similarity	NPC470224
0.8942	High Similarity	NPC5284
0.8942	High Similarity	NPC101450
0.8932	High Similarity	NPC258323
0.8922	High Similarity	NPC472655
0.8922	High Similarity	NPC96377
0.8911	High Similarity	NPC140723
0.8835	High Similarity	NPC255387
0.8835	High Similarity	NPC131665
0.88	High Similarity	NPC167974
0.8776	High Similarity	NPC279974
0.8774	High Similarity	NPC280782
0.8774	High Similarity	NPC207251
0.8725	High Similarity	NPC36688
0.8704	High Similarity	NPC49492
0.8704	High Similarity	NPC266728
0.87	High Similarity	NPC119036
0.87	High Similarity	NPC477854
0.8692	High Similarity	NPC250109
0.8667	High Similarity	NPC5475
0.8667	High Similarity	NPC173905
0.8667	High Similarity	NPC284828
0.8667	High Similarity	NPC472216
0.866	High Similarity	NPC189520
0.8646	High Similarity	NPC475921
0.8646	High Similarity	NPC474704
0.8627	High Similarity	NPC473928
0.8611	High Similarity	NPC326542
0.8571	High Similarity	NPC472219
0.8571	High Similarity	NPC472218
0.8571	High Similarity	NPC472217
0.8571	High Similarity	NPC19412
0.8571	High Similarity	NPC477855
0.8558	High Similarity	NPC196528
0.8558	High Similarity	NPC102352
0.8557	High Similarity	NPC471896
0.8544	High Similarity	NPC191892
0.8544	High Similarity	NPC471005
0.8542	High Similarity	NPC250687
0.8542	High Similarity	NPC229407
0.8542	High Similarity	NPC254572
0.8542	High Similarity	NPC48824
0.8529	High Similarity	NPC477052
0.8529	High Similarity	NPC477051
0.8529	High Similarity	NPC477053
0.8519	High Similarity	NPC962
0.8519	High Similarity	NPC52634
0.85	High Similarity	NPC477853
0.85	High Similarity	NPC173272
0.8485	Intermediate Similarity	NPC240617
0.8476	Intermediate Similarity	NPC144854
0.8476	Intermediate Similarity	NPC220974
0.8476	Intermediate Similarity	NPC3316
0.8476	Intermediate Similarity	NPC230541
0.8469	Intermediate Similarity	NPC471747
0.8462	Intermediate Similarity	NPC472228
0.8462	Intermediate Similarity	NPC85593
0.8462	Intermediate Similarity	NPC472227
0.8462	Intermediate Similarity	NPC100955
0.8462	Intermediate Similarity	NPC121566
0.8462	Intermediate Similarity	NPC31430
0.8462	Intermediate Similarity	NPC477812
0.8455	Intermediate Similarity	NPC284068
0.8454	Intermediate Similarity	NPC269267
0.8447	Intermediate Similarity	NPC22388
0.8447	Intermediate Similarity	NPC477054
0.844	Intermediate Similarity	NPC117712
0.8438	Intermediate Similarity	NPC142361
0.8438	Intermediate Similarity	NPC474684
0.8438	Intermediate Similarity	NPC167877
0.8431	Intermediate Similarity	NPC83709
0.8431	Intermediate Similarity	NPC316964
0.8426	Intermediate Similarity	NPC234042
0.8426	Intermediate Similarity	NPC152117
0.8421	Intermediate Similarity	NPC8369
0.8416	Intermediate Similarity	NPC253586
0.8411	Intermediate Similarity	NPC470065
0.8411	Intermediate Similarity	NPC239097
0.8407	Intermediate Similarity	NPC222688
0.84	Intermediate Similarity	NPC48330
0.84	Intermediate Similarity	NPC469599
0.8396	Intermediate Similarity	NPC277017
0.8396	Intermediate Similarity	NPC154608
0.8396	Intermediate Similarity	NPC192813
0.8393	Intermediate Similarity	NPC109973
0.8384	Intermediate Similarity	NPC470376
0.8384	Intermediate Similarity	NPC170220
0.8384	Intermediate Similarity	NPC141497
0.8384	Intermediate Similarity	NPC470375
0.8384	Intermediate Similarity	NPC107674
0.8381	Intermediate Similarity	NPC278628
0.8381	Intermediate Similarity	NPC63023
0.8381	Intermediate Similarity	NPC95243
0.8381	Intermediate Similarity	NPC470587
0.8381	Intermediate Similarity	NPC231530
0.8367	Intermediate Similarity	NPC289213
0.8367	Intermediate Similarity	NPC473269
0.8367	Intermediate Similarity	NPC148414
0.8367	Intermediate Similarity	NPC175628
0.8367	Intermediate Similarity	NPC111585
0.8365	Intermediate Similarity	NPC264048
0.8364	Intermediate Similarity	NPC40632
0.8364	Intermediate Similarity	NPC474734
0.8364	Intermediate Similarity	NPC96312
0.8364	Intermediate Similarity	NPC251236
0.8364	Intermediate Similarity	NPC328374
0.8364	Intermediate Similarity	NPC196931
0.8364	Intermediate Similarity	NPC207217
0.835	Intermediate Similarity	NPC289670
0.8349	Intermediate Similarity	NPC49451
0.8349	Intermediate Similarity	NPC317210
0.8349	Intermediate Similarity	NPC194100
0.8349	Intermediate Similarity	NPC178981
0.8349	Intermediate Similarity	NPC255017
0.8333	Intermediate Similarity	NPC153792
0.8333	Intermediate Similarity	NPC263827
0.8333	Intermediate Similarity	NPC271387
0.8333	Intermediate Similarity	NPC250481
0.8333	Intermediate Similarity	NPC285410
0.8333	Intermediate Similarity	NPC73038
0.8333	Intermediate Similarity	NPC114274
0.8318	Intermediate Similarity	NPC41405
0.8318	Intermediate Similarity	NPC153239
0.8318	Intermediate Similarity	NPC143706
0.8318	Intermediate Similarity	NPC472534
0.8318	Intermediate Similarity	NPC141350
0.8318	Intermediate Similarity	NPC310546
0.8318	Intermediate Similarity	NPC218853
0.8317	Intermediate Similarity	NPC49371
0.8317	Intermediate Similarity	NPC256227
0.8304	Intermediate Similarity	NPC477071
0.8304	Intermediate Similarity	NPC475041
0.8302	Intermediate Similarity	NPC293512
0.8302	Intermediate Similarity	NPC165873
0.8302	Intermediate Similarity	NPC473037
0.8302	Intermediate Similarity	NPC83744
0.8302	Intermediate Similarity	NPC477916
0.83	Intermediate Similarity	NPC174051
0.83	Intermediate Similarity	NPC470957
0.83	Intermediate Similarity	NPC470958
0.83	Intermediate Similarity	NPC67831
0.83	Intermediate Similarity	NPC159410
0.8288	Intermediate Similarity	NPC473590
0.8286	Intermediate Similarity	NPC204833
0.8286	Intermediate Similarity	NPC475036
0.8286	Intermediate Similarity	NPC209502
0.8286	Intermediate Similarity	NPC29705
0.8286	Intermediate Similarity	NPC75531
0.8286	Intermediate Similarity	NPC149124
0.8286	Intermediate Similarity	NPC301787
0.8283	Intermediate Similarity	NPC110657
0.8283	Intermediate Similarity	NPC26888
0.8283	Intermediate Similarity	NPC212301
0.8283	Intermediate Similarity	NPC262870
0.8283	Intermediate Similarity	NPC86266
0.8283	Intermediate Similarity	NPC297265
0.8273	Intermediate Similarity	NPC473798
0.8273	Intermediate Similarity	NPC243354
0.8273	Intermediate Similarity	NPC471398
0.8269	Intermediate Similarity	NPC193934
0.8269	Intermediate Similarity	NPC124544
0.8269	Intermediate Similarity	NPC136289
0.8269	Intermediate Similarity	NPC473163
0.8269	Intermediate Similarity	NPC271980
0.8269	Intermediate Similarity	NPC475558
0.8269	Intermediate Similarity	NPC473788
0.8265	Intermediate Similarity	NPC32830
0.8265	Intermediate Similarity	NPC474889
0.8265	Intermediate Similarity	NPC476733
0.8265	Intermediate Similarity	NPC215029
0.8257	Intermediate Similarity	NPC474516
0.8257	Intermediate Similarity	NPC472002
0.8257	Intermediate Similarity	NPC269530
0.8257	Intermediate Similarity	NPC126691
0.8257	Intermediate Similarity	NPC470063
0.8252	Intermediate Similarity	NPC218383
0.8252	Intermediate Similarity	NPC477655
0.8252	Intermediate Similarity	NPC108371
0.8247	Intermediate Similarity	NPC90652
0.8247	Intermediate Similarity	NPC159046
0.8247	Intermediate Similarity	NPC251808
0.8247	Intermediate Similarity	NPC233836
0.8247	Intermediate Similarity	NPC187376
0.8247	Intermediate Similarity	NPC474174
0.8246	Intermediate Similarity	NPC65858
0.8241	Intermediate Similarity	NPC475134
0.8241	Intermediate Similarity	NPC76084
0.8241	Intermediate Similarity	NPC475563
0.8241	Intermediate Similarity	NPC129340
0.8235	Intermediate Similarity	NPC108078
0.8235	Intermediate Similarity	NPC210337
0.8235	Intermediate Similarity	NPC475032
0.8235	Intermediate Similarity	NPC475033
0.8235	Intermediate Similarity	NPC475894
0.823	Intermediate Similarity	NPC476961
0.8224	Intermediate Similarity	NPC295389
0.8224	Intermediate Similarity	NPC329417
0.8224	Intermediate Similarity	NPC94529

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 NPC471293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1498
0.2-0.3	4020
0.3-0.4	2273
0.4-0.5	667
0.5-0.6	199
0.6-0.7	167
0.7-0.8	131
0.8-0.85	25
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8396	Intermediate Similarity	NPD7320	Approved
0.8381	Intermediate Similarity	NPD6675	Approved
0.8381	Intermediate Similarity	NPD7128	Approved
0.8381	Intermediate Similarity	NPD5739	Approved
0.8381	Intermediate Similarity	NPD6402	Approved
0.8318	Intermediate Similarity	NPD6372	Approved
0.8318	Intermediate Similarity	NPD6373	Approved
0.8257	Intermediate Similarity	NPD8297	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD6881	Approved
0.8208	Intermediate Similarity	NPD6008	Approved
0.82	Intermediate Similarity	NPD6399	Phase 3
0.8182	Intermediate Similarity	NPD4632	Approved
0.8165	Intermediate Similarity	NPD6649	Approved
0.8165	Intermediate Similarity	NPD6650	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8131	Intermediate Similarity	NPD5701	Approved
0.8103	Intermediate Similarity	NPD7492	Approved
0.8081	Intermediate Similarity	NPD5328	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.807	Intermediate Similarity	NPD6059	Approved
0.807	Intermediate Similarity	NPD6054	Approved
0.807	Intermediate Similarity	NPD6319	Approved
0.8034	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.7966	Intermediate Similarity	NPD7078	Approved
0.7966	Intermediate Similarity	NPD8293	Discontinued
0.7965	Intermediate Similarity	NPD7115	Discovery
0.7931	Intermediate Similarity	NPD6370	Approved
0.7928	Intermediate Similarity	NPD6882	Approved
0.7921	Intermediate Similarity	NPD6079	Approved
0.7899	Intermediate Similarity	NPD7736	Approved
0.789	Intermediate Similarity	NPD6011	Approved
0.7885	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6083	Phase 2
0.7885	Intermediate Similarity	NPD4755	Approved
0.7881	Intermediate Similarity	NPD7507	Approved
0.7864	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6015	Approved
0.7845	Intermediate Similarity	NPD6016	Approved
0.7838	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7638	Approved
0.7807	Intermediate Similarity	NPD6009	Approved
0.7788	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD5988	Approved
0.7755	Intermediate Similarity	NPD4786	Approved
0.7748	Intermediate Similarity	NPD4634	Approved
0.7745	Intermediate Similarity	NPD8034	Phase 2
0.7745	Intermediate Similarity	NPD8035	Phase 2
0.7736	Intermediate Similarity	NPD4700	Approved
0.7736	Intermediate Similarity	NPD4696	Approved
0.7736	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD7639	Approved
0.7736	Intermediate Similarity	NPD7640	Approved
0.7736	Intermediate Similarity	NPD5286	Approved
0.7712	Intermediate Similarity	NPD7604	Phase 2
0.7692	Intermediate Similarity	NPD5983	Phase 2
0.7686	Intermediate Similarity	NPD7319	Approved
0.7677	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5696	Approved
0.7636	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5221	Approved
0.7619	Intermediate Similarity	NPD5222	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7593	Intermediate Similarity	NPD5224	Approved
0.7593	Intermediate Similarity	NPD5225	Approved
0.7593	Intermediate Similarity	NPD4633	Approved
0.7593	Intermediate Similarity	NPD5226	Approved
0.7593	Intermediate Similarity	NPD5211	Phase 2
0.7583	Intermediate Similarity	NPD6336	Discontinued
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7568	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6274	Approved
0.7551	Intermediate Similarity	NPD3667	Approved
0.7547	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD5173	Approved
0.7542	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5695	Phase 3
0.7523	Intermediate Similarity	NPD5174	Approved
0.7523	Intermediate Similarity	NPD5175	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4202	Approved
0.7477	Intermediate Similarity	NPD4225	Approved
0.7459	Intermediate Similarity	NPD6033	Approved
0.7455	Intermediate Similarity	NPD5141	Approved
0.7451	Intermediate Similarity	NPD6672	Approved
0.7451	Intermediate Similarity	NPD6903	Approved
0.7451	Intermediate Similarity	NPD5737	Approved
0.7436	Intermediate Similarity	NPD6335	Approved
0.7429	Intermediate Similarity	NPD6001	Approved
0.7426	Intermediate Similarity	NPD7146	Approved
0.7426	Intermediate Similarity	NPD5330	Approved
0.7426	Intermediate Similarity	NPD6409	Approved
0.7426	Intermediate Similarity	NPD6684	Approved
0.7426	Intermediate Similarity	NPD7334	Approved
0.7426	Intermediate Similarity	NPD7521	Approved
0.7417	Intermediate Similarity	NPD8328	Phase 3
0.7414	Intermediate Similarity	NPD6868	Approved
0.7404	Intermediate Similarity	NPD6411	Approved
0.7395	Intermediate Similarity	NPD6908	Approved
0.7395	Intermediate Similarity	NPD6909	Approved
0.7387	Intermediate Similarity	NPD4767	Approved
0.7387	Intermediate Similarity	NPD4768	Approved
0.7379	Intermediate Similarity	NPD4753	Phase 2
0.7364	Intermediate Similarity	NPD4754	Approved
0.735	Intermediate Similarity	NPD6317	Approved
0.735	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7525	Registered
0.732	Intermediate Similarity	NPD6697	Approved
0.732	Intermediate Similarity	NPD6118	Approved
0.732	Intermediate Similarity	NPD6115	Approved
0.732	Intermediate Similarity	NPD6114	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7288	Intermediate Similarity	NPD6314	Approved
0.7288	Intermediate Similarity	NPD7327	Approved
0.7288	Intermediate Similarity	NPD6313	Approved
0.7288	Intermediate Similarity	NPD7328	Approved
0.7282	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6686	Approved
0.7257	Intermediate Similarity	NPD5128	Approved
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD6098	Approved
0.7241	Intermediate Similarity	NPD8133	Approved
0.7228	Intermediate Similarity	NPD3133	Approved
0.7228	Intermediate Similarity	NPD3665	Phase 1
0.7228	Intermediate Similarity	NPD3666	Approved
0.7227	Intermediate Similarity	NPD7516	Approved
0.7212	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6080	Approved
0.7212	Intermediate Similarity	NPD6904	Approved
0.7212	Intermediate Similarity	NPD6101	Approved
0.7212	Intermediate Similarity	NPD6673	Approved
0.7196	Intermediate Similarity	NPD4629	Approved
0.7196	Intermediate Similarity	NPD5210	Approved
0.7184	Intermediate Similarity	NPD3573	Approved
0.7184	Intermediate Similarity	NPD7524	Approved
0.717	Intermediate Similarity	NPD5779	Approved
0.717	Intermediate Similarity	NPD5778	Approved
0.7167	Intermediate Similarity	NPD8377	Approved
0.7167	Intermediate Similarity	NPD8294	Approved
0.7143	Intermediate Similarity	NPD5207	Approved
0.7131	Intermediate Similarity	NPD6067	Discontinued
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.7117	Intermediate Similarity	NPD7632	Discontinued
0.7113	Intermediate Similarity	NPD6117	Approved
0.7107	Intermediate Similarity	NPD8335	Approved
0.7107	Intermediate Similarity	NPD8379	Approved
0.7107	Intermediate Similarity	NPD8378	Approved
0.7107	Intermediate Similarity	NPD8296	Approved
0.7107	Intermediate Similarity	NPD8380	Approved
0.7107	Intermediate Similarity	NPD8033	Approved
0.7087	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7637	Suspended
0.7075	Intermediate Similarity	NPD5284	Approved
0.7075	Intermediate Similarity	NPD5281	Approved
0.7069	Intermediate Similarity	NPD5215	Approved
0.7069	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD6116	Phase 1
0.703	Intermediate Similarity	NPD4223	Phase 3
0.703	Intermediate Similarity	NPD4221	Approved
0.7018	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD7339	Approved
0.699	Remote Similarity	NPD5329	Approved
0.6983	Remote Similarity	NPD5169	Approved
0.6983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5135	Approved
0.6967	Remote Similarity	NPD7503	Approved
0.6967	Remote Similarity	NPD8513	Phase 3
0.6967	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6961	Remote Similarity	NPD6695	Phase 3
0.6957	Remote Similarity	NPD5168	Approved
0.6952	Remote Similarity	NPD5208	Approved
0.6923	Remote Similarity	NPD5127	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