NPASS Compound

Structure

NPC171598 OpenBabel07101718322D 35 37 0 0 1 0 0 0 0 0999 V2000 -6.7520 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 2.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7005 -0.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5157 3.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6991 -0.5577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6220 -2.9950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3441 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5157 0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3178 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8309 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 -0.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3276 2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2915 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 0.0805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3276 4.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.3684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9705 -2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 3.0016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3276 1.5410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 1.5410 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1708 0.0805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3960 0.8895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9684 0.1018 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8573 1.0542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1708 1.0542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3276 5.4358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9524 0.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 -2.4739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3276 -0.4063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 3.9752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3484 1.0919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2714 -1.3454 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 9 2 0 0 0 0 2 15 2 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 8 31 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 16 26 1 6 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 27 1 6 0 0 0 23 31 1 0 0 0 0 24 33 1 6 0 0 0 24 35 1 0 0 0 0 25 27 1 6 0 0 0 25 34 1 0 0 0 0 25 35 1 0 0 0 0 26 7 1 1 0 0 0 27 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.26
Volume:	504.382
LogP:	2.998
LogD:	2.417
LogS:	-4.218
# Rotatable Bonds:	11
TPSA:	97.36
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	5.729
Fsp3:	0.667
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:	-4.789
MDCK Permeability:	6.27366898697801e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	71.36034393310547%
Volume Distribution (VD):	2.071
Pgp-substrate:	38.565792083740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	2.761
Half-life (T1/2):	0.403

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.889
Carcinogencity:	0.086
Eye Corrosion:	0.034
Eye Irritation:	0.04
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC171598

Natural Product ID:	NPC171598
*Common Name:**	Casearlucin B
IUPAC Name:	[(1R,3S,5R,6aR,7S,8S,10R,10aR)-1,3-diacetyloxy-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	BZVDIOLNPIHYMD-FIHQBSKBSA-N
Standard InCHI:	InChI=1S/C27H38O8/c1-9-15(2)10-11-26(7)16(3)12-23(31-8)27-21(13-20(14-22(26)27)32-17(4)28)24(33-18(5)29)35-25(27)34-19(6)30/h9,13,16,20,22-25H,1-2,10-12,14H2,3-8H3/t16-,20-,22+,23+,24+,25-,26-,27-/m0/s1
SMILES:	C=CC(=C)CC[C@@]1(C)[C@@H](C)C[C@H]([C@]23C(=C[C@@H](C[C@H]12)OC(=O)C)[C@H](OC(=O)C)O[C@@H]3OC(=O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419877
PubChem CID:	73352260
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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	13300.0	nM	PMID[485988]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7100.0	nM	PMID[485988]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	6200.0	nM	PMID[485988]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	4300.0	nM	PMID[485988]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	4700.0	nM	PMID[485988]

☑ 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 NPC171598 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	213
0.1-0.2	1291
0.2-0.3	4528
0.3-0.4	10352
0.4-0.5	11778
0.5-0.6	7701
0.6-0.7	5650
0.7-0.8	1056
0.8-0.85	25
0.85-0.9	46
0.9-0.95	37
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC472189
0.9888	High Similarity	NPC471362
0.9888	High Similarity	NPC471372
0.978	High Similarity	NPC318917
0.978	High Similarity	NPC472186
0.978	High Similarity	NPC476800
0.978	High Similarity	NPC471366
0.9674	High Similarity	NPC472187
0.9674	High Similarity	NPC473204
0.9674	High Similarity	NPC473545
0.967	High Similarity	NPC472188
0.9368	High Similarity	NPC127933
0.9368	High Similarity	NPC7644
0.9368	High Similarity	NPC7613
0.9368	High Similarity	NPC475889
0.9271	High Similarity	NPC473207
0.9271	High Similarity	NPC81567
0.9271	High Similarity	NPC201880
0.9271	High Similarity	NPC470321
0.9271	High Similarity	NPC264867
0.9263	High Similarity	NPC471363
0.9263	High Similarity	NPC238397
0.9167	High Similarity	NPC134270
0.914	High Similarity	NPC94905
0.914	High Similarity	NPC8954
0.913	High Similarity	NPC88507
0.9082	High Similarity	NPC125423
0.9082	High Similarity	NPC88013
0.9082	High Similarity	NPC109376
0.9082	High Similarity	NPC184512
0.899	High Similarity	NPC135015
0.899	High Similarity	NPC470024
0.899	High Similarity	NPC311223
0.899	High Similarity	NPC217921
0.899	High Similarity	NPC48548
0.899	High Similarity	NPC128795
0.899	High Similarity	NPC224660
0.898	High Similarity	NPC252296
0.898	High Similarity	NPC172867
0.8936	High Similarity	NPC311166
0.89	High Similarity	NPC40728
0.89	High Similarity	NPC316974
0.8842	High Similarity	NPC98112
0.8812	High Similarity	NPC316708
0.8812	High Similarity	NPC119550
0.8788	High Similarity	NPC218158
0.8725	High Similarity	NPC17791
0.8725	High Similarity	NPC470026
0.866	High Similarity	NPC477968
0.866	High Similarity	NPC219285
0.866	High Similarity	NPC228251
0.866	High Similarity	NPC477972
0.866	High Similarity	NPC477971
0.866	High Similarity	NPC161527
0.866	High Similarity	NPC20113
0.8641	High Similarity	NPC328074
0.8641	High Similarity	NPC317460
0.8641	High Similarity	NPC470025
0.8641	High Similarity	NPC321272
0.8586	High Similarity	NPC132395
0.8586	High Similarity	NPC471365
0.8586	High Similarity	NPC120009
0.8586	High Similarity	NPC471364
0.8571	High Similarity	NPC102996
0.8558	High Similarity	NPC470027
0.8556	High Similarity	NPC471367
0.8495	Intermediate Similarity	NPC470819
0.8495	Intermediate Similarity	NPC293044
0.8478	Intermediate Similarity	NPC102640
0.8404	Intermediate Similarity	NPC470817
0.8387	Intermediate Similarity	NPC69713
0.837	Intermediate Similarity	NPC471368
0.837	Intermediate Similarity	NPC471369
0.8247	Intermediate Similarity	NPC477970
0.8247	Intermediate Similarity	NPC135224
0.8247	Intermediate Similarity	NPC477969
0.8247	Intermediate Similarity	NPC100892
0.8211	Intermediate Similarity	NPC469403
0.82	Intermediate Similarity	NPC280991
0.8191	Intermediate Similarity	NPC263079
0.8173	Intermediate Similarity	NPC112457
0.8173	Intermediate Similarity	NPC206618
0.8172	Intermediate Similarity	NPC118266
0.8172	Intermediate Similarity	NPC323209
0.8155	Intermediate Similarity	NPC475074
0.8155	Intermediate Similarity	NPC472390
0.8144	Intermediate Similarity	NPC477722
0.8144	Intermediate Similarity	NPC140277
0.8144	Intermediate Similarity	NPC189513
0.8137	Intermediate Similarity	NPC470768
0.8113	Intermediate Similarity	NPC473125
0.8111	Intermediate Similarity	NPC469802
0.8111	Intermediate Similarity	NPC473685
0.8105	Intermediate Similarity	NPC261320
0.8105	Intermediate Similarity	NPC246028
0.81	Intermediate Similarity	NPC324841
0.8081	Intermediate Similarity	NPC125551
0.8081	Intermediate Similarity	NPC309503
0.8081	Intermediate Similarity	NPC239547
0.8081	Intermediate Similarity	NPC96597
0.8081	Intermediate Similarity	NPC91197
0.8081	Intermediate Similarity	NPC155319
0.8077	Intermediate Similarity	NPC38948
0.8065	Intermediate Similarity	NPC472442
0.8061	Intermediate Similarity	NPC286612
0.8061	Intermediate Similarity	NPC230347
0.8061	Intermediate Similarity	NPC275310
0.8058	Intermediate Similarity	NPC470763
0.8058	Intermediate Similarity	NPC470767
0.8058	Intermediate Similarity	NPC239961
0.8058	Intermediate Similarity	NPC82251
0.8043	Intermediate Similarity	NPC472440
0.8041	Intermediate Similarity	NPC163902
0.8041	Intermediate Similarity	NPC12297
0.8039	Intermediate Similarity	NPC471885
0.8039	Intermediate Similarity	NPC471886
0.8039	Intermediate Similarity	NPC471888
0.8039	Intermediate Similarity	NPC471450
0.8039	Intermediate Similarity	NPC45897
0.8039	Intermediate Similarity	NPC471887
0.8037	Intermediate Similarity	NPC44298
0.8037	Intermediate Similarity	NPC40133
0.8037	Intermediate Similarity	NPC290608
0.8037	Intermediate Similarity	NPC49413
0.8037	Intermediate Similarity	NPC473128
0.8022	Intermediate Similarity	NPC25554
0.8021	Intermediate Similarity	NPC471371
0.8021	Intermediate Similarity	NPC471370
0.8021	Intermediate Similarity	NPC220216
0.802	Intermediate Similarity	NPC198992
0.802	Intermediate Similarity	NPC472554
0.8	Intermediate Similarity	NPC473154
0.8	Intermediate Similarity	NPC106332
0.8	Intermediate Similarity	NPC474440
0.8	Intermediate Similarity	NPC473879
0.8	Intermediate Similarity	NPC477128
0.8	Intermediate Similarity	NPC477928
0.7981	Intermediate Similarity	NPC293512
0.798	Intermediate Similarity	NPC165632
0.798	Intermediate Similarity	NPC194132
0.798	Intermediate Similarity	NPC284194
0.798	Intermediate Similarity	NPC475380
0.798	Intermediate Similarity	NPC221801
0.798	Intermediate Similarity	NPC211810
0.798	Intermediate Similarity	NPC209297
0.798	Intermediate Similarity	NPC471765
0.7961	Intermediate Similarity	NPC222161
0.7959	Intermediate Similarity	NPC472360
0.7959	Intermediate Similarity	NPC472416
0.7941	Intermediate Similarity	NPC471482
0.7941	Intermediate Similarity	NPC300399
0.7941	Intermediate Similarity	NPC11956
0.7941	Intermediate Similarity	NPC475344
0.7941	Intermediate Similarity	NPC476471
0.7941	Intermediate Similarity	NPC472552
0.7941	Intermediate Similarity	NPC37207
0.7941	Intermediate Similarity	NPC470571
0.7941	Intermediate Similarity	NPC471889
0.7938	Intermediate Similarity	NPC474631
0.7938	Intermediate Similarity	NPC124374
0.7938	Intermediate Similarity	NPC477574
0.7935	Intermediate Similarity	NPC471218
0.7925	Intermediate Similarity	NPC177047
0.7921	Intermediate Similarity	NPC470761
0.7921	Intermediate Similarity	NPC473219
0.79	Intermediate Similarity	NPC198549
0.79	Intermediate Similarity	NPC473244
0.79	Intermediate Similarity	NPC475446
0.79	Intermediate Similarity	NPC100912
0.79	Intermediate Similarity	NPC311241
0.79	Intermediate Similarity	NPC113976
0.7895	Intermediate Similarity	NPC471779
0.7895	Intermediate Similarity	NPC166857
0.7885	Intermediate Similarity	NPC51719
0.7879	Intermediate Similarity	NPC276110
0.7879	Intermediate Similarity	NPC37603
0.7879	Intermediate Similarity	NPC471786
0.7872	Intermediate Similarity	NPC119001
0.787	Intermediate Similarity	NPC264153
0.787	Intermediate Similarity	NPC157441
0.787	Intermediate Similarity	NPC293658
0.787	Intermediate Similarity	NPC474410
0.7864	Intermediate Similarity	NPC474124
0.7864	Intermediate Similarity	NPC281378
0.7864	Intermediate Similarity	NPC23584
0.7857	Intermediate Similarity	NPC99653
0.7857	Intermediate Similarity	NPC472812
0.7857	Intermediate Similarity	NPC204731
0.7857	Intermediate Similarity	NPC7349
0.7843	Intermediate Similarity	NPC475617
0.7843	Intermediate Similarity	NPC477717
0.7843	Intermediate Similarity	NPC475767
0.7843	Intermediate Similarity	NPC119467
0.7838	Intermediate Similarity	NPC122971
0.7838	Intermediate Similarity	NPC470914
0.7822	Intermediate Similarity	NPC107806
0.7822	Intermediate Similarity	NPC72647
0.7818	Intermediate Similarity	NPC203862
0.7812	Intermediate Similarity	NPC93411
0.781	Intermediate Similarity	NPC33053

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 NPC171598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1484
0.2-0.3	3956
0.3-0.4	2334
0.4-0.5	761
0.5-0.6	295
0.6-0.7	133
0.7-0.8	11
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
0.7544	Intermediate Similarity	NPD7503	Approved
0.7434	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7328	Approved
0.7407	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7368	Intermediate Similarity	NPD7516	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7241	Intermediate Similarity	NPD8296	Approved
0.7241	Intermediate Similarity	NPD8380	Approved
0.7241	Intermediate Similarity	NPD8379	Approved
0.7241	Intermediate Similarity	NPD8378	Approved
0.7241	Intermediate Similarity	NPD8335	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD8517	Approved
0.7094	Intermediate Similarity	NPD8513	Phase 3
0.7094	Intermediate Similarity	NPD8516	Approved
0.7094	Intermediate Similarity	NPD8515	Approved
0.7075	Intermediate Similarity	NPD6648	Approved
0.7041	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.697	Remote Similarity	NPD1694	Approved
0.6875	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5344	Discontinued
0.6847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7319	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6731	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD7838	Discovery
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8328	Phase 3
0.6535	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8293	Discontinued
0.6532	Remote Similarity	NPD8074	Phase 3
0.6504	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8039	Approved
0.6452	Remote Similarity	NPD6616	Approved
0.6449	Remote Similarity	NPD7748	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6444	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6695	Phase 3
0.6422	Remote Similarity	NPD7902	Approved
0.6415	Remote Similarity	NPD6411	Approved
0.6408	Remote Similarity	NPD6684	Approved
0.6408	Remote Similarity	NPD7521	Approved
0.6408	Remote Similarity	NPD6409	Approved
0.6408	Remote Similarity	NPD7334	Approved
0.6408	Remote Similarity	NPD7146	Approved
0.6408	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6333	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD6698	Approved
0.6321	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD7525	Registered
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6373	Approved
0.629	Remote Similarity	NPD6067	Discontinued
0.6289	Remote Similarity	NPD8264	Approved
0.6286	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6672	Approved
0.6286	Remote Similarity	NPD6903	Approved
0.6286	Remote Similarity	NPD5737	Approved
0.6271	Remote Similarity	NPD6053	Discontinued
0.6271	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD7515	Phase 2
0.6261	Remote Similarity	NPD5697	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD6015	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6101	Approved
0.621	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6929	Approved
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD7750	Discontinued
0.619	Remote Similarity	NPD3573	Approved
0.619	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6319	Approved
0.6168	Remote Similarity	NPD3168	Discontinued
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD7332	Phase 2
0.6139	Remote Similarity	NPD6930	Phase 2
0.6139	Remote Similarity	NPD7514	Phase 3
0.6122	Remote Similarity	NPD6942	Approved
0.6122	Remote Similarity	NPD7339	Approved
0.6121	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD8034	Phase 2
0.6111	Remote Similarity	NPD8035	Phase 2
0.6111	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD7983	Approved
0.61	Remote Similarity	NPD7145	Approved
0.6095	Remote Similarity	NPD4249	Approved
0.6083	Remote Similarity	NPD4632	Approved
0.6078	Remote Similarity	NPD6902	Approved
0.6077	Remote Similarity	NPD7260	Phase 2
0.6075	Remote Similarity	NPD1695	Approved
0.6068	Remote Similarity	NPD6011	Approved
0.6061	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4786	Approved
0.6058	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7839	Suspended
0.6019	Remote Similarity	NPD5209	Approved
0.6019	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.5983	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6083	Phase 2
0.5982	Remote Similarity	NPD6084	Phase 2
0.598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6079	Approved
0.5963	Remote Similarity	NPD6050	Approved
0.5963	Remote Similarity	NPD7087	Discontinued
0.5963	Remote Similarity	NPD5694	Approved
0.5946	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5695	Phase 3
0.5943	Remote Similarity	NPD3618	Phase 1
0.5943	Remote Similarity	NPD6098	Approved
0.5929	Remote Similarity	NPD7625	Phase 1
0.5926	Remote Similarity	NPD5328	Approved
0.5926	Remote Similarity	NPD6673	Approved
0.5926	Remote Similarity	NPD6080	Approved
0.5926	Remote Similarity	NPD6904	Approved
0.5917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5211	Phase 2
0.5906	Remote Similarity	NPD7604	Phase 2
0.5877	Remote Similarity	NPD5285	Approved
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5872	Remote Similarity	NPD5692	Phase 3
0.5859	Remote Similarity	NPD6926	Approved
0.5859	Remote Similarity	NPD6924	Approved
0.5856	Remote Similarity	NPD5282	Discontinued
0.5856	Remote Similarity	NPD6001	Approved
0.5851	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6893	Approved
0.5849	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6033	Approved
0.5841	Remote Similarity	NPD4755	Approved
0.584	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD6371	Approved
0.5827	Remote Similarity	NPD5126	Approved
0.5827	Remote Similarity	NPD5125	Phase 3
0.5825	Remote Similarity	NPD4819	Approved
0.5825	Remote Similarity	NPD4821	Approved
0.5825	Remote Similarity	NPD4820	Approved
0.5825	Remote Similarity	NPD7509	Discontinued
0.5825	Remote Similarity	NPD4822	Approved
0.5818	Remote Similarity	NPD5281	Approved
0.5818	Remote Similarity	NPD5284	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