NPASS Compound

Structure

NPC469994 OpenBabel07101719512D 33 36 0 0 1 0 0 0 0 0999 V2000 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 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 -0.4067 -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 2.2382 -2.4680 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 2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 -3.6270 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 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 -2.5981 0.5000 0.0000 C 0 0 1 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 4.1945 -2.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 11 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 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 19 3 1 1 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 26 29 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	5.613
LogD:	4.776
LogS:	-4.966
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	5.014
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.984
MDCK Permeability:	1.3316544936969876e-05
Pgp-inhibitor:	0.884
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.882
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	93.26313018798828%
Volume Distribution (VD):	1.17
Pgp-substrate:	7.7607645988464355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.492
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.457
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.833

ADMET: Excretion

Clearance (CL):	8.753
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.336
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.813
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.056
Carcinogencity:	0.239
Eye Corrosion:	0.004
Eye Irritation:	0.02
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: NPC469994

Natural Product ID:	NPC469994
*Common Name:**	Meliastatin 5
IUPAC Name:	(5R,9R,10R,13S,14S,16S,17S)-16-hydroxy-17-[(2R)-5-hydroxy-6-methylhept-6-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Meliastatin 5
Standard InCHIKey:	ZTTLEOUJUZYDTO-BWVGTCNCSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(2)22(31)11-9-19(3)26-23(32)17-30(8)21-10-12-24-27(4,5)25(33)14-15-28(24,6)20(21)13-16-29(26,30)7/h10,19-20,22-24,26,31-32H,1,9,11-17H2,2-8H3/t19-,20+,22?,23+,24+,26-,28-,29+,30-/m1/s1
SMILES:	CC(CCC(C(=C)C)O)C1C(CC2(C1(CCC3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641927
PubChem CID:	53319209
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
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502333]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18596	Melia dubia	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
ED50	2
IC50	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.7	ug ml-1	PMID[515358]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.7	ug ml-1	PMID[515359]
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	9.5	ug.mL-1	PMID[515359]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16.0	ug.mL-1	PMID[515359]

☑ 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 NPC469994 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	152
0.1-0.2	1072
0.2-0.3	5207
0.3-0.4	15560
0.4-0.5	7309
0.5-0.6	6058
0.6-0.7	4808
0.7-0.8	2047
0.8-0.85	348
0.85-0.9	104
0.9-0.95	26
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC82902
0.9639	High Similarity	NPC2983
0.9634	High Similarity	NPC317590
0.963	High Similarity	NPC474218
0.963	High Similarity	NPC471224
0.939	High Similarity	NPC474083
0.9294	High Similarity	NPC69622
0.9294	High Similarity	NPC320026
0.9286	High Similarity	NPC328313
0.9268	High Similarity	NPC214043
0.9268	High Similarity	NPC85774
0.9268	High Similarity	NPC59453
0.9268	High Similarity	NPC221758
0.9268	High Similarity	NPC227064
0.9268	High Similarity	NPC161423
0.9268	High Similarity	NPC329043
0.9268	High Similarity	NPC58841
0.9268	High Similarity	NPC321187
0.9176	High Similarity	NPC477943
0.9176	High Similarity	NPC76879
0.9176	High Similarity	NPC473999
0.9176	High Similarity	NPC309603
0.908	High Similarity	NPC472942
0.907	High Similarity	NPC48010
0.907	High Similarity	NPC171441
0.9048	High Similarity	NPC31564
0.9048	High Similarity	NPC51014
0.9048	High Similarity	NPC474733
0.9048	High Similarity	NPC474778
0.9048	High Similarity	NPC145879
0.9048	High Similarity	NPC474732
0.9036	High Similarity	NPC165064
0.9036	High Similarity	NPC473246
0.9024	High Similarity	NPC151519
0.8966	High Similarity	NPC154101
0.8966	High Similarity	NPC473998
0.8966	High Similarity	NPC475806
0.8953	High Similarity	NPC472970
0.8953	High Similarity	NPC472971
0.8941	High Similarity	NPC58063
0.8941	High Similarity	NPC475740
0.8941	High Similarity	NPC90652
0.8929	High Similarity	NPC469948
0.8889	High Similarity	NPC107243
0.8889	High Similarity	NPC475894
0.8876	High Similarity	NPC472932
0.8864	High Similarity	NPC474736
0.8864	High Similarity	NPC243866
0.8837	High Similarity	NPC470417
0.8824	High Similarity	NPC155011
0.8824	High Similarity	NPC473168
0.8824	High Similarity	NPC327115
0.8824	High Similarity	NPC20688
0.881	High Similarity	NPC237712
0.8795	High Similarity	NPC477858
0.8795	High Similarity	NPC46881
0.8795	High Similarity	NPC193347
0.8795	High Similarity	NPC145143
0.878	High Similarity	NPC472478
0.8778	High Similarity	NPC155676
0.8765	High Similarity	NPC477514
0.8765	High Similarity	NPC82635
0.8764	High Similarity	NPC8993
0.8764	High Similarity	NPC111015
0.8736	High Similarity	NPC326627
0.8736	High Similarity	NPC268406
0.8736	High Similarity	NPC32830
0.8736	High Similarity	NPC31985
0.8736	High Similarity	NPC26959
0.8736	High Similarity	NPC310010
0.8736	High Similarity	NPC474245
0.8736	High Similarity	NPC1015
0.8736	High Similarity	NPC54689
0.8736	High Similarity	NPC186688
0.8721	High Similarity	NPC96496
0.8721	High Similarity	NPC93778
0.8721	High Similarity	NPC472484
0.8721	High Similarity	NPC142361
0.8721	High Similarity	NPC472481
0.8721	High Similarity	NPC472482
0.8721	High Similarity	NPC474684
0.8706	High Similarity	NPC470574
0.8706	High Similarity	NPC274724
0.8696	High Similarity	NPC218383
0.8696	High Similarity	NPC154072
0.869	High Similarity	NPC470047
0.869	High Similarity	NPC278648
0.869	High Similarity	NPC476082
0.869	High Similarity	NPC472498
0.869	High Similarity	NPC470046
0.8681	High Similarity	NPC57416
0.8675	High Similarity	NPC474484
0.8675	High Similarity	NPC147066
0.8675	High Similarity	NPC103754
0.8667	High Similarity	NPC469599
0.8667	High Similarity	NPC271195
0.8659	High Similarity	NPC215843
0.8652	High Similarity	NPC69454
0.8652	High Similarity	NPC470376
0.8652	High Similarity	NPC250575
0.8652	High Similarity	NPC152897
0.8652	High Similarity	NPC470375
0.8652	High Similarity	NPC472930
0.8652	High Similarity	NPC66429
0.8621	High Similarity	NPC193360
0.8621	High Similarity	NPC53911
0.8621	High Similarity	NPC471722
0.8621	High Similarity	NPC328539
0.8605	High Similarity	NPC94755
0.8605	High Similarity	NPC89077
0.8605	High Similarity	NPC222613
0.8605	High Similarity	NPC475022
0.8605	High Similarity	NPC118648
0.8605	High Similarity	NPC72133
0.8605	High Similarity	NPC470955
0.8588	High Similarity	NPC263974
0.8588	High Similarity	NPC472265
0.8588	High Similarity	NPC144258
0.8588	High Similarity	NPC194937
0.8588	High Similarity	NPC473157
0.8588	High Similarity	NPC476038
0.8587	High Similarity	NPC197386
0.8587	High Similarity	NPC166745
0.8587	High Similarity	NPC235464
0.8571	High Similarity	NPC49371
0.8571	High Similarity	NPC170985
0.8556	High Similarity	NPC292793
0.8554	High Similarity	NPC2482
0.8539	High Similarity	NPC272746
0.8539	High Similarity	NPC63748
0.8539	High Similarity	NPC233116
0.8539	High Similarity	NPC262870
0.8537	High Similarity	NPC474216
0.8537	High Similarity	NPC477522
0.8523	High Similarity	NPC155479
0.8523	High Similarity	NPC215029
0.8523	High Similarity	NPC86319
0.8523	High Similarity	NPC472475
0.8523	High Similarity	NPC475921
0.8523	High Similarity	NPC275740
0.8523	High Similarity	NPC472477
0.8523	High Similarity	NPC476733
0.8523	High Similarity	NPC474704
0.8519	High Similarity	NPC247325
0.8519	High Similarity	NPC244488
0.8511	High Similarity	NPC477915
0.8511	High Similarity	NPC87351
0.8506	High Similarity	NPC187376
0.8506	High Similarity	NPC312215
0.8506	High Similarity	NPC159046
0.8506	High Similarity	NPC233836
0.8506	High Similarity	NPC136948
0.8506	High Similarity	NPC136548
0.8488	Intermediate Similarity	NPC283733
0.8488	Intermediate Similarity	NPC292553
0.8488	Intermediate Similarity	NPC202868
0.8478	Intermediate Similarity	NPC190554
0.8471	Intermediate Similarity	NPC245866
0.8462	Intermediate Similarity	NPC476174
0.8462	Intermediate Similarity	NPC263347
0.8462	Intermediate Similarity	NPC259286
0.8452	Intermediate Similarity	NPC4166
0.8452	Intermediate Similarity	NPC38350
0.8452	Intermediate Similarity	NPC201912
0.8452	Intermediate Similarity	NPC6434
0.8452	Intermediate Similarity	NPC3915
0.8444	Intermediate Similarity	NPC475255
0.8444	Intermediate Similarity	NPC477520
0.8444	Intermediate Similarity	NPC109305
0.8444	Intermediate Similarity	NPC206810
0.8444	Intermediate Similarity	NPC233118
0.8434	Intermediate Similarity	NPC477371
0.8434	Intermediate Similarity	NPC143182
0.8434	Intermediate Similarity	NPC28862
0.8434	Intermediate Similarity	NPC47982
0.8434	Intermediate Similarity	NPC84694
0.8434	Intermediate Similarity	NPC109546
0.8434	Intermediate Similarity	NPC1319
0.8434	Intermediate Similarity	NPC30986
0.8434	Intermediate Similarity	NPC209430
0.8434	Intermediate Similarity	NPC201459
0.8434	Intermediate Similarity	NPC81306
0.8434	Intermediate Similarity	NPC472490
0.8427	Intermediate Similarity	NPC469400
0.8427	Intermediate Similarity	NPC85173
0.8427	Intermediate Similarity	NPC191684
0.8427	Intermediate Similarity	NPC126993
0.8421	Intermediate Similarity	NPC26478
0.8421	Intermediate Similarity	NPC311612
0.8415	Intermediate Similarity	NPC74995
0.8409	Intermediate Similarity	NPC472483
0.8409	Intermediate Similarity	NPC44181
0.8409	Intermediate Similarity	NPC471724
0.8409	Intermediate Similarity	NPC143767
0.8409	Intermediate Similarity	NPC131470
0.8409	Intermediate Similarity	NPC28227
0.8409	Intermediate Similarity	NPC294480
0.8404	Intermediate Similarity	NPC474327
0.8391	Intermediate Similarity	NPC212843
0.8391	Intermediate Similarity	NPC470050

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 NPC469994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1390
0.2-0.3	4120
0.3-0.4	2443
0.4-0.5	566
0.5-0.6	165
0.6-0.7	118
0.7-0.8	142
0.8-0.85	46
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9268	High Similarity	NPD3666	Approved
0.9268	High Similarity	NPD4786	Approved
0.9268	High Similarity	NPD3665	Phase 1
0.9268	High Similarity	NPD3133	Approved
0.9024	High Similarity	NPD3667	Approved
0.8795	High Similarity	NPD4223	Phase 3
0.8795	High Similarity	NPD4221	Approved
0.8736	High Similarity	NPD5328	Approved
0.8736	High Similarity	NPD4753	Phase 2
0.8706	High Similarity	NPD5329	Approved
0.8652	High Similarity	NPD4202	Approved
0.8605	High Similarity	NPD3618	Phase 1
0.8588	High Similarity	NPD4197	Approved
0.8539	High Similarity	NPD6079	Approved
0.8471	Intermediate Similarity	NPD4788	Approved
0.8391	Intermediate Similarity	NPD5330	Approved
0.8391	Intermediate Similarity	NPD4689	Approved
0.8391	Intermediate Similarity	NPD7334	Approved
0.8391	Intermediate Similarity	NPD6409	Approved
0.8391	Intermediate Similarity	NPD7146	Approved
0.8391	Intermediate Similarity	NPD4693	Phase 3
0.8391	Intermediate Similarity	NPD4138	Approved
0.8391	Intermediate Similarity	NPD5205	Approved
0.8391	Intermediate Similarity	NPD4690	Approved
0.8391	Intermediate Similarity	NPD7521	Approved
0.8391	Intermediate Similarity	NPD4688	Approved
0.8391	Intermediate Similarity	NPD6684	Approved
0.8391	Intermediate Similarity	NPD5279	Phase 3
0.8316	Intermediate Similarity	NPD5211	Phase 2
0.8293	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4755	Approved
0.828	Intermediate Similarity	NPD6083	Phase 2
0.828	Intermediate Similarity	NPD6084	Phase 2
0.8261	Intermediate Similarity	NPD5210	Approved
0.8261	Intermediate Similarity	NPD4629	Approved
0.8242	Intermediate Similarity	NPD6399	Phase 3
0.8202	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6903	Approved
0.8182	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4694	Approved
0.8182	Intermediate Similarity	NPD5690	Phase 2
0.8171	Intermediate Similarity	NPD7339	Approved
0.8171	Intermediate Similarity	NPD6942	Approved
0.8161	Intermediate Similarity	NPD3668	Phase 3
0.8144	Intermediate Similarity	NPD5141	Approved
0.8105	Intermediate Similarity	NPD5285	Approved
0.8105	Intermediate Similarity	NPD4696	Approved
0.8105	Intermediate Similarity	NPD5286	Approved
0.8105	Intermediate Similarity	NPD4700	Approved
0.8025	Intermediate Similarity	NPD4243	Approved
0.8023	Intermediate Similarity	NPD4692	Approved
0.8023	Intermediate Similarity	NPD4139	Approved
0.8021	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD4195	Approved
0.7979	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD5222	Approved
0.7979	Intermediate Similarity	NPD4697	Phase 3
0.7978	Intermediate Similarity	NPD6098	Approved
0.7938	Intermediate Similarity	NPD5225	Approved
0.7938	Intermediate Similarity	NPD4633	Approved
0.7938	Intermediate Similarity	NPD5224	Approved
0.7938	Intermediate Similarity	NPD5226	Approved
0.7901	Intermediate Similarity	NPD4244	Approved
0.7901	Intermediate Similarity	NPD4245	Approved
0.7895	Intermediate Similarity	NPD5173	Approved
0.7889	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3617	Approved
0.7879	Intermediate Similarity	NPD7128	Approved
0.7879	Intermediate Similarity	NPD5739	Approved
0.7879	Intermediate Similarity	NPD6675	Approved
0.7879	Intermediate Similarity	NPD6402	Approved
0.7872	Intermediate Similarity	NPD5695	Phase 3
0.7865	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5174	Approved
0.7857	Intermediate Similarity	NPD4754	Approved
0.7857	Intermediate Similarity	NPD5175	Approved
0.7831	Intermediate Similarity	NPD4784	Approved
0.7831	Intermediate Similarity	NPD4785	Approved
0.7812	Intermediate Similarity	NPD5696	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.7802	Intermediate Similarity	NPD5737	Approved
0.7778	Intermediate Similarity	NPD3698	Phase 2
0.7778	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4519	Discontinued
0.7778	Intermediate Similarity	NPD4623	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD7515	Phase 2
0.7742	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD6899	Approved
0.7723	Intermediate Similarity	NPD7320	Approved
0.7723	Intermediate Similarity	NPD6881	Approved
0.7717	Intermediate Similarity	NPD6904	Approved
0.7717	Intermediate Similarity	NPD6673	Approved
0.7717	Intermediate Similarity	NPD6080	Approved
0.7701	Intermediate Similarity	NPD7525	Registered
0.77	Intermediate Similarity	NPD4768	Approved
0.77	Intermediate Similarity	NPD4767	Approved
0.7683	Intermediate Similarity	NPD4747	Approved
0.7674	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6372	Approved
0.7647	Intermediate Similarity	NPD6373	Approved
0.7634	Intermediate Similarity	NPD4096	Approved
0.7624	Intermediate Similarity	NPD5701	Approved
0.7624	Intermediate Similarity	NPD6412	Phase 2
0.7624	Intermediate Similarity	NPD5697	Approved
0.7619	Intermediate Similarity	NPD6924	Approved
0.7619	Intermediate Similarity	NPD6926	Approved
0.7609	Intermediate Similarity	NPD5208	Approved
0.759	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6929	Approved
0.7573	Intermediate Similarity	NPD6883	Approved
0.7573	Intermediate Similarity	NPD7290	Approved
0.7573	Intermediate Similarity	NPD7102	Approved
0.7561	Intermediate Similarity	NPD4137	Phase 3
0.7553	Intermediate Similarity	NPD5693	Phase 1
0.7551	Intermediate Similarity	NPD7640	Approved
0.7551	Intermediate Similarity	NPD7639	Approved
0.7549	Intermediate Similarity	NPD4729	Approved
0.7549	Intermediate Similarity	NPD5128	Approved
0.7549	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD4730	Approved
0.7529	Intermediate Similarity	NPD5275	Approved
0.7529	Intermediate Similarity	NPD4190	Phase 3
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6930	Phase 2
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7476	Intermediate Similarity	NPD6012	Approved
0.7476	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD6013	Approved
0.7474	Intermediate Similarity	NPD5133	Approved
0.747	Intermediate Similarity	NPD4789	Approved
0.747	Intermediate Similarity	NPD4691	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7444	Intermediate Similarity	NPD5362	Discontinued
0.7442	Intermediate Similarity	NPD6933	Approved
0.7439	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6882	Approved
0.7429	Intermediate Similarity	NPD8297	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7412	Intermediate Similarity	NPD5733	Approved
0.7404	Intermediate Similarity	NPD5249	Phase 3
0.7404	Intermediate Similarity	NPD5247	Approved
0.7404	Intermediate Similarity	NPD5135	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD5251	Approved
0.7404	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5250	Approved
0.7404	Intermediate Similarity	NPD5169	Approved
0.7404	Intermediate Similarity	NPD5248	Approved
0.7396	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7356	Intermediate Similarity	NPD5776	Phase 2
0.7356	Intermediate Similarity	NPD6925	Approved
0.7349	Intermediate Similarity	NPD6923	Approved
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6922	Approved
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6051	Approved
0.7333	Intermediate Similarity	NPD4270	Approved
0.7333	Intermediate Similarity	NPD5216	Approved
0.7333	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD5215	Approved
0.7333	Intermediate Similarity	NPD5127	Approved
0.7333	Intermediate Similarity	NPD5217	Approved
0.7303	Intermediate Similarity	NPD4748	Discontinued
0.7273	Intermediate Similarity	NPD7145	Approved
0.7263	Intermediate Similarity	NPD5207	Approved
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7262	Intermediate Similarity	NPD7144	Approved
0.7262	Intermediate Similarity	NPD7143	Approved
0.7253	Intermediate Similarity	NPD6695	Phase 3
0.7228	Intermediate Similarity	NPD5091	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7212	Intermediate Similarity	NPD5168	Approved
0.7209	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4687	Approved
0.7209	Intermediate Similarity	NPD4058	Approved
0.7196	Intermediate Similarity	NPD4632	Approved
0.7191	Intermediate Similarity	NPD7645	Phase 2
0.7188	Intermediate Similarity	NPD5694	Approved
0.7188	Intermediate Similarity	NPD8035	Phase 2
0.7188	Intermediate Similarity	NPD8034	Phase 2
0.7176	Intermediate Similarity	NPD7151	Approved
0.7176	Intermediate Similarity	NPD7150	Approved
0.7176	Intermediate Similarity	NPD5276	Approved
0.7176	Intermediate Similarity	NPD7152	Approved
0.7174	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7902	Approved
0.7156	Intermediate Similarity	NPD7115	Discovery

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