NPASS Compound

Structure

NPC472187 OpenBabel07101719252D 40 42 0 0 1 0 0 0 0 0999 V2000 -2.0562 -2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7732 -0.6343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2091 3.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7965 1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5173 3.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7121 -0.4076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0213 -2.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3546 1.9034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5173 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3580 -1.2853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7965 -0.6343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3632 4.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7044 -0.5594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3314 0.2116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8430 1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0204 -0.4076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3286 2.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0204 2.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3081 0.2116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5173 3.9877 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8662 0.0808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9767 -2.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1745 3.0110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3286 1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0204 1.5459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1745 0.0808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0062 0.3695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3286 4.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3973 0.8923 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9714 0.1021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8662 1.0575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1745 1.0575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6303 -3.0044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9616 0.5726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3286 5.4528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3286 -0.4076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2785 -1.3496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1745 3.9877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3527 1.0954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 2 0 0 0 0 3 12 1 0 0 0 0 4 19 2 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 9 36 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 31 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 24 2 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 20 28 1 0 0 0 0 21 31 1 6 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 38 1 6 0 0 0 24 29 1 0 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 26 32 1 6 0 0 0 26 36 1 0 0 0 0 27 34 2 0 0 0 0 27 39 1 0 0 0 0 28 35 2 0 0 0 0 28 38 1 0 0 0 0 29 39 1 6 0 0 0 29 40 1 0 0 0 0 30 32 1 6 0 0 0 30 37 1 0 0 0 0 30 40 1 0 0 0 0 31 8 1 1 0 0 0 32 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.33
Volume:	590.862
LogP:	5.214
LogD:	4.158
LogS:	-5.811
# Rotatable Bonds:	15
TPSA:	97.36
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	5.854
Fsp3:	0.719
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:	-4.683
MDCK Permeability:	3.74755181837827e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.305
30% Bioavailability (F30%):	0.487

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	86.4040298461914%
Volume Distribution (VD):	2.337
Pgp-substrate:	6.473741054534912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.494
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.532

ADMET: Excretion

Clearance (CL):	4.948
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.745
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.815
Carcinogencity:	0.43
Eye Corrosion:	0.014
Eye Irritation:	0.022
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC472187

Natural Product ID:	NPC472187
*Common Name:**	MVCWMFXWYJCOSR-IPMXAIJNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MVCWMFXWYJCOSR-IPMXAIJNSA-N
Standard InCHI:	InChI=1S/C32H48O8/c1-10-13-27(34)39-29-24-17-23(38-28(35)20(5)12-3)18-25-31(8,15-14-19(4)11-2)21(6)16-26(36-9)32(24,25)30(40-29)37-22(7)33/h11,17,20-21,23,25-26,29-30H,2,4,10,12-16,18H2,1,3,5-9H3/t20?,21-,23+,25+,26+,29+,30-,31-,32-/m1/s1
SMILES:	CCCC(=O)OC1C2=CC(CC3C2(C(CC(C3(C)CCC(=C)C=C)C)OC)C(O1)OC(=O)C)OC(=O)C(C)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3343970
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	=	12.7	ug.mL-1	PMID[475027]

☑ 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 NPC472187 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	223
0.1-0.2	1193
0.2-0.3	4390
0.3-0.4	9455
0.4-0.5	12577
0.5-0.6	7499
0.6-0.7	6010
0.7-0.8	1223
0.8-0.85	26
0.85-0.9	30
0.9-0.95	50
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473545
0.9891	High Similarity	NPC472186
0.9891	High Similarity	NPC471366
0.9891	High Similarity	NPC318917
0.9891	High Similarity	NPC476800
0.9785	High Similarity	NPC473204
0.9783	High Similarity	NPC472188
0.9674	High Similarity	NPC171598
0.9565	High Similarity	NPC471372
0.9565	High Similarity	NPC471362
0.9565	High Similarity	NPC472189
0.9479	High Similarity	NPC7613
0.9479	High Similarity	NPC127933
0.9479	High Similarity	NPC7644
0.9479	High Similarity	NPC475889
0.9381	High Similarity	NPC470321
0.9381	High Similarity	NPC473207
0.9381	High Similarity	NPC264867
0.9381	High Similarity	NPC81567
0.9381	High Similarity	NPC201880
0.9375	High Similarity	NPC471363
0.9375	High Similarity	NPC238397
0.9278	High Similarity	NPC134270
0.9247	High Similarity	NPC88507
0.92	High Similarity	NPC40728
0.9192	High Similarity	NPC88013
0.9192	High Similarity	NPC184512
0.9192	High Similarity	NPC125423
0.91	High Similarity	NPC217921
0.91	High Similarity	NPC128795
0.91	High Similarity	NPC311223
0.91	High Similarity	NPC48548
0.91	High Similarity	NPC135015
0.9091	High Similarity	NPC252296
0.9053	High Similarity	NPC311166
0.901	High Similarity	NPC316974
0.9	High Similarity	NPC109376
0.8922	High Similarity	NPC119550
0.8911	High Similarity	NPC470024
0.8911	High Similarity	NPC224660
0.89	High Similarity	NPC172867
0.8854	High Similarity	NPC8954
0.8854	High Similarity	NPC94905
0.8738	High Similarity	NPC316708
0.8713	High Similarity	NPC218158
0.87	High Similarity	NPC132395
0.87	High Similarity	NPC471364
0.87	High Similarity	NPC471365
0.8654	High Similarity	NPC470026
0.8654	High Similarity	NPC17791
0.8571	High Similarity	NPC328074
0.8571	High Similarity	NPC321272
0.8571	High Similarity	NPC470025
0.8571	High Similarity	NPC317460
0.8571	High Similarity	NPC98112
0.8511	High Similarity	NPC69713
0.8491	Intermediate Similarity	NPC470027
0.8404	Intermediate Similarity	NPC102640
0.84	Intermediate Similarity	NPC228251
0.84	Intermediate Similarity	NPC477971
0.84	Intermediate Similarity	NPC477972
0.84	Intermediate Similarity	NPC161527
0.84	Intermediate Similarity	NPC20113
0.84	Intermediate Similarity	NPC477968
0.84	Intermediate Similarity	NPC219285
0.8333	Intermediate Similarity	NPC120009
0.8298	Intermediate Similarity	NPC102996
0.8286	Intermediate Similarity	NPC112457
0.828	Intermediate Similarity	NPC471367
0.8229	Intermediate Similarity	NPC470819
0.8229	Intermediate Similarity	NPC293044
0.82	Intermediate Similarity	NPC100912
0.8144	Intermediate Similarity	NPC471371
0.8144	Intermediate Similarity	NPC471370
0.8144	Intermediate Similarity	NPC470817
0.8125	Intermediate Similarity	NPC204731
0.8125	Intermediate Similarity	NPC477128
0.8119	Intermediate Similarity	NPC107806
0.8119	Intermediate Similarity	NPC72647
0.8119	Intermediate Similarity	NPC473154
0.8105	Intermediate Similarity	NPC471369
0.8105	Intermediate Similarity	NPC471368
0.8095	Intermediate Similarity	NPC472390
0.8095	Intermediate Similarity	NPC293512
0.8077	Intermediate Similarity	NPC222161
0.8077	Intermediate Similarity	NPC470768
0.8061	Intermediate Similarity	NPC477574
0.8061	Intermediate Similarity	NPC474631
0.8056	Intermediate Similarity	NPC473125
0.8039	Intermediate Similarity	NPC473219
0.8039	Intermediate Similarity	NPC470761
0.8037	Intermediate Similarity	NPC83005
0.802	Intermediate Similarity	NPC311241
0.802	Intermediate Similarity	NPC475446
0.8018	Intermediate Similarity	NPC473617
0.8018	Intermediate Similarity	NPC473828
0.8	Intermediate Similarity	NPC135224
0.8	Intermediate Similarity	NPC477970
0.8	Intermediate Similarity	NPC471786
0.8	Intermediate Similarity	NPC470767
0.8	Intermediate Similarity	NPC82251
0.8	Intermediate Similarity	NPC37603
0.8	Intermediate Similarity	NPC477969
0.8	Intermediate Similarity	NPC239961
0.8	Intermediate Similarity	NPC470763
0.8	Intermediate Similarity	NPC100892
0.7982	Intermediate Similarity	NPC75167
0.7982	Intermediate Similarity	NPC290608
0.7982	Intermediate Similarity	NPC49413
0.7982	Intermediate Similarity	NPC264153
0.7982	Intermediate Similarity	NPC44298
0.7982	Intermediate Similarity	NPC473128
0.7982	Intermediate Similarity	NPC41129
0.7982	Intermediate Similarity	NPC157441
0.7982	Intermediate Similarity	NPC474410
0.7982	Intermediate Similarity	NPC311592
0.7982	Intermediate Similarity	NPC40133
0.7982	Intermediate Similarity	NPC293658
0.7981	Intermediate Similarity	NPC471885
0.7981	Intermediate Similarity	NPC471888
0.7981	Intermediate Similarity	NPC471886
0.7981	Intermediate Similarity	NPC471887
0.798	Intermediate Similarity	NPC99653
0.7961	Intermediate Similarity	NPC280991
0.7961	Intermediate Similarity	NPC198992
0.7959	Intermediate Similarity	NPC469403
0.7946	Intermediate Similarity	NPC470914
0.7946	Intermediate Similarity	NPC477071
0.7946	Intermediate Similarity	NPC122971
0.7944	Intermediate Similarity	NPC206618
0.7941	Intermediate Similarity	NPC474440
0.7938	Intermediate Similarity	NPC473879
0.7938	Intermediate Similarity	NPC263079
0.7925	Intermediate Similarity	NPC475074
0.7921	Intermediate Similarity	NPC112654
0.7921	Intermediate Similarity	NPC209297
0.7921	Intermediate Similarity	NPC475380
0.7921	Intermediate Similarity	NPC165632
0.7921	Intermediate Similarity	NPC73858
0.7917	Intermediate Similarity	NPC323209
0.7917	Intermediate Similarity	NPC118266
0.7909	Intermediate Similarity	NPC181145
0.79	Intermediate Similarity	NPC189513
0.79	Intermediate Similarity	NPC477129
0.79	Intermediate Similarity	NPC140277
0.79	Intermediate Similarity	NPC477722
0.79	Intermediate Similarity	NPC477130
0.789	Intermediate Similarity	NPC194951
0.789	Intermediate Similarity	NPC12046
0.7885	Intermediate Similarity	NPC472552
0.7885	Intermediate Similarity	NPC475344
0.7885	Intermediate Similarity	NPC37207
0.7885	Intermediate Similarity	NPC476471
0.7879	Intermediate Similarity	NPC65513
0.7879	Intermediate Similarity	NPC124374
0.7876	Intermediate Similarity	NPC151616
0.7864	Intermediate Similarity	NPC324841
0.7857	Intermediate Similarity	NPC246028
0.7857	Intermediate Similarity	NPC261320
0.785	Intermediate Similarity	NPC38948
0.7849	Intermediate Similarity	NPC473685
0.7849	Intermediate Similarity	NPC469802
0.7843	Intermediate Similarity	NPC309503
0.7843	Intermediate Similarity	NPC155319
0.7843	Intermediate Similarity	NPC125551
0.7843	Intermediate Similarity	NPC96597
0.7843	Intermediate Similarity	NPC239547
0.7843	Intermediate Similarity	NPC91197
0.7843	Intermediate Similarity	NPC110937
0.7838	Intermediate Similarity	NPC207637
0.783	Intermediate Similarity	NPC476760
0.783	Intermediate Similarity	NPC476761
0.783	Intermediate Similarity	NPC476762
0.7822	Intermediate Similarity	NPC286612
0.7822	Intermediate Similarity	NPC230347
0.7822	Intermediate Similarity	NPC275310
0.7818	Intermediate Similarity	NPC473159
0.7812	Intermediate Similarity	NPC472442
0.781	Intermediate Similarity	NPC471450
0.781	Intermediate Similarity	NPC45897
0.781	Intermediate Similarity	NPC474124
0.781	Intermediate Similarity	NPC254202
0.781	Intermediate Similarity	NPC23584
0.7807	Intermediate Similarity	NPC476204
0.7807	Intermediate Similarity	NPC170084
0.78	Intermediate Similarity	NPC163902
0.78	Intermediate Similarity	NPC12297
0.7789	Intermediate Similarity	NPC472440
0.7788	Intermediate Similarity	NPC472554
0.7778	Intermediate Similarity	NPC48732
0.7778	Intermediate Similarity	NPC220216
0.7768	Intermediate Similarity	NPC473405
0.7768	Intermediate Similarity	NPC23046
0.7767	Intermediate Similarity	NPC216478
0.7767	Intermediate Similarity	NPC477928
0.7766	Intermediate Similarity	NPC25554
0.7757	Intermediate Similarity	NPC33053
0.7755	Intermediate Similarity	NPC106332
0.7748	Intermediate Similarity	NPC220293
0.7748	Intermediate Similarity	NPC475163

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 NPC472187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1439
0.2-0.3	3897
0.3-0.4	2385
0.4-0.5	790
0.5-0.6	288
0.6-0.7	160
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7523	Intermediate Similarity	NPD6686	Approved
0.7429	Intermediate Similarity	NPD7638	Approved
0.7358	Intermediate Similarity	NPD7639	Approved
0.7358	Intermediate Similarity	NPD7640	Approved
0.735	Intermediate Similarity	NPD8515	Approved
0.735	Intermediate Similarity	NPD8513	Phase 3
0.735	Intermediate Similarity	NPD8033	Approved
0.735	Intermediate Similarity	NPD7503	Approved
0.735	Intermediate Similarity	NPD8517	Approved
0.735	Intermediate Similarity	NPD8516	Approved
0.7265	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD8377	Approved
0.7241	Intermediate Similarity	NPD7328	Approved
0.7241	Intermediate Similarity	NPD7327	Approved
0.7203	Intermediate Similarity	NPD8380	Approved
0.7203	Intermediate Similarity	NPD8335	Approved
0.7203	Intermediate Similarity	NPD8379	Approved
0.7203	Intermediate Similarity	NPD8296	Approved
0.7203	Intermediate Similarity	NPD8378	Approved
0.7179	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7507	Approved
0.7103	Intermediate Similarity	NPD4225	Approved
0.71	Intermediate Similarity	NPD1694	Approved
0.7043	Intermediate Similarity	NPD8133	Approved
0.6964	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7319	Approved
0.6887	Remote Similarity	NPD7900	Approved
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6648	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7637	Suspended
0.6855	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6051	Approved
0.6814	Remote Similarity	NPD6412	Phase 2
0.681	Remote Similarity	NPD6882	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.68	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6399	Phase 3
0.6792	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8293	Discontinued
0.6774	Remote Similarity	NPD8074	Phase 3
0.6771	Remote Similarity	NPD8039	Approved
0.6762	Remote Similarity	NPD7838	Discovery
0.6757	Remote Similarity	NPD7632	Discontinued
0.6729	Remote Similarity	NPD7748	Approved
0.6724	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6370	Approved
0.6697	Remote Similarity	NPD7902	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6613	Remote Similarity	NPD7492	Approved
0.6583	Remote Similarity	NPD7115	Discovery
0.656	Remote Similarity	NPD6616	Approved
0.6557	Remote Similarity	NPD6054	Approved
0.6542	Remote Similarity	NPD6411	Approved
0.6538	Remote Similarity	NPD7521	Approved
0.6538	Remote Similarity	NPD5330	Approved
0.6538	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD6409	Approved
0.6538	Remote Similarity	NPD7146	Approved
0.6525	Remote Similarity	NPD8297	Approved
0.6508	Remote Similarity	NPD7078	Approved
0.6466	Remote Similarity	NPD6899	Approved
0.6466	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD6698	Approved
0.6449	Remote Similarity	NPD46	Approved
0.6446	Remote Similarity	NPD6009	Approved
0.6441	Remote Similarity	NPD6649	Approved
0.6441	Remote Similarity	NPD8130	Phase 1
0.6441	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD7128	Approved
0.6435	Remote Similarity	NPD6675	Approved
0.6435	Remote Similarity	NPD6402	Approved
0.6435	Remote Similarity	NPD5739	Approved
0.6423	Remote Similarity	NPD6059	Approved
0.6415	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6672	Approved
0.641	Remote Similarity	NPD6372	Approved
0.641	Remote Similarity	NPD6373	Approved
0.64	Remote Similarity	NPD6067	Discontinued
0.6389	Remote Similarity	NPD7515	Phase 2
0.6389	Remote Similarity	NPD8034	Phase 2
0.6389	Remote Similarity	NPD8035	Phase 2
0.6389	Remote Similarity	NPD7983	Approved
0.6387	Remote Similarity	NPD6053	Discontinued
0.6379	Remote Similarity	NPD5697	Approved
0.6371	Remote Similarity	NPD6015	Approved
0.6371	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6883	Approved
0.6356	Remote Similarity	NPD7102	Approved
0.6356	Remote Similarity	NPD7290	Approved
0.6355	Remote Similarity	NPD6101	Approved
0.6355	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD4251	Approved
0.6321	Remote Similarity	NPD4250	Approved
0.632	Remote Similarity	NPD5988	Approved
0.6306	Remote Similarity	NPD7839	Suspended
0.6303	Remote Similarity	NPD6617	Approved
0.6303	Remote Similarity	NPD6847	Approved
0.6303	Remote Similarity	NPD6869	Approved
0.629	Remote Similarity	NPD6319	Approved
0.6271	Remote Similarity	NPD6014	Approved
0.6271	Remote Similarity	NPD6013	Approved
0.6271	Remote Similarity	NPD6012	Approved
0.6263	Remote Similarity	NPD8264	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5693	Phase 1
0.6239	Remote Similarity	NPD5701	Approved
0.6237	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4249	Approved
0.6204	Remote Similarity	NPD1695	Approved
0.6198	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD4786	Approved
0.619	Remote Similarity	NPD3668	Phase 3
0.6186	Remote Similarity	NPD6011	Approved
0.6183	Remote Similarity	NPD7260	Phase 2
0.6176	Remote Similarity	NPD7645	Phase 2
0.6168	Remote Similarity	NPD7750	Discontinued
0.6154	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD3667	Approved
0.6147	Remote Similarity	NPD5207	Approved
0.6117	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7525	Registered
0.6106	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD6050	Approved
0.6091	Remote Similarity	NPD6079	Approved
0.6091	Remote Similarity	NPD5694	Approved
0.6075	Remote Similarity	NPD3618	Phase 1
0.6075	Remote Similarity	NPD6098	Approved
0.6071	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5695	Phase 3
0.6055	Remote Similarity	NPD6673	Approved
0.6055	Remote Similarity	NPD6080	Approved
0.6055	Remote Similarity	NPD5328	Approved
0.6055	Remote Similarity	NPD6904	Approved
0.6047	Remote Similarity	NPD8451	Approved
0.6034	Remote Similarity	NPD5211	Phase 2
0.6033	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7524	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6016	Remote Similarity	NPD7829	Approved
0.6016	Remote Similarity	NPD7830	Approved
0.6015	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD8444	Approved
0.5982	Remote Similarity	NPD5282	Discontinued
0.5982	Remote Similarity	NPD6001	Approved
0.5981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4755	Approved
0.5962	Remote Similarity	NPD7332	Phase 2
0.5962	Remote Similarity	NPD4821	Approved
0.5962	Remote Similarity	NPD4820	Approved
0.5962	Remote Similarity	NPD6930	Phase 2
0.5962	Remote Similarity	NPD4822	Approved
0.5962	Remote Similarity	NPD4819	Approved
0.5962	Remote Similarity	NPD6931	Approved
0.5962	Remote Similarity	NPD7514	Phase 3
0.5954	Remote Similarity	NPD8336	Approved
0.5954	Remote Similarity	NPD8337	Approved
0.5954	Remote Similarity	NPD6033	Approved
0.5952	Remote Similarity	NPD7101	Approved
0.5952	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD6371	Approved
0.5946	Remote Similarity	NPD5284	Approved
0.5946	Remote Similarity	NPD5281	Approved
0.5943	Remote Similarity	NPD3669	Approved
0.5943	Remote Similarity	NPD7154	Phase 3
0.5943	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6942	Approved
0.5941	Remote Similarity	NPD7339	Approved
0.5932	Remote Similarity	NPD5141	Approved
0.5923	Remote Similarity	NPD6336	Discontinued
0.5922	Remote Similarity	NPD4271	Approved
0.5922	Remote Similarity	NPD7145	Approved
0.5922	Remote Similarity	NPD4268	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