NPASS Compound

Structure

CID208839 OpenBabel06191716002D 35 37 0 0 1 0 0 0 0 0999 V2000 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 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 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 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 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 16 1 0 0 0 0 4 17 2 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 33 1 0 0 0 0 17 21 1 0 0 0 0 18 5 1 6 0 0 0 19 18 1 6 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 6 0 0 0 21 30 1 6 0 0 0 22 14 1 6 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 23 33 1 0 0 0 0 24 16 1 1 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 28 1 0 0 0 0 26 34 1 0 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.31
Volume:	518.16
LogP:	3.955
LogD:	3.78
LogS:	-3.175
# Rotatable Bonds:	10
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	6.282
Fsp3:	0.786
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:	-4.77
MDCK Permeability:	0.00012291937309782952
Pgp-inhibitor:	0.022
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.557
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	89.32905578613281%
Volume Distribution (VD):	0.898
Pgp-substrate:	5.178279399871826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	9.151
Half-life (T1/2):	0.693

ADMET: Toxicity

hERG Blockers:	0.442
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.139
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.63

Download Data

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

Natural Product: NPC208839

Natural Product ID:	NPC208839
*Common Name:**	Hirsutalin A
IUPAC Name:	n.a.
Synonyms:	Hirsutalin A
Standard InCHIKey:	LGCBXJHPKWYGGG-ZEOQMOKSSA-N
Standard InCHI:	InChI=1S/C28H44O7/c1-7-9-23(31)33-15-18(5)19-11-10-16(3)24-22-14-17(4)21(30)12-13-28(6,26(34-22)25(19)24)35-27(32)20(29)8-2/h10,18-22,24-26,29-30H,4,7-9,11-15H2,1-3,5-6H3/t18-,19+,20+,21-,22+,24+,25+,26+,28+/m0/s1
SMILES:	CCCC(=O)OC[C@@H]([C@H]1CC=C([C@H]2[C@@H]1[C@H]1O[C@@H]2CC(=C)[C@H](CC[C@@]1(C)OC(=O)[C@@H](CC)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631447
PubChem CID:	50900038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane 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
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20979397]
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28000.0	nM	PMID[575699]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	35000.0	nM	PMID[575699]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29000.0	nM	PMID[575699]

☑ 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 NPC208839 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	179
0.1-0.2	1156
0.2-0.3	4860
0.3-0.4	13740
0.4-0.5	10410
0.5-0.6	7887
0.6-0.7	4030
0.7-0.8	422
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC309656
0.8966	High Similarity	NPC321812
0.8966	High Similarity	NPC322922
0.8621	High Similarity	NPC239308
0.8605	High Similarity	NPC77003
0.8556	High Similarity	NPC92370
0.8462	Intermediate Similarity	NPC291875
0.8427	Intermediate Similarity	NPC196911
0.8427	Intermediate Similarity	NPC471379
0.8409	Intermediate Similarity	NPC5958
0.8391	Intermediate Similarity	NPC118116
0.837	Intermediate Similarity	NPC312471
0.837	Intermediate Similarity	NPC471378
0.8333	Intermediate Similarity	NPC475684
0.8295	Intermediate Similarity	NPC103171
0.8247	Intermediate Similarity	NPC272223
0.8242	Intermediate Similarity	NPC44538
0.8152	Intermediate Similarity	NPC470260
0.8152	Intermediate Similarity	NPC75443
0.8152	Intermediate Similarity	NPC476724
0.8152	Intermediate Similarity	NPC476723
0.814	Intermediate Similarity	NPC40049
0.81	Intermediate Similarity	NPC258532
0.8085	Intermediate Similarity	NPC122057
0.8085	Intermediate Similarity	NPC312805
0.8065	Intermediate Similarity	NPC161560
0.8023	Intermediate Similarity	NPC329626
0.8021	Intermediate Similarity	NPC476720
0.7938	Intermediate Similarity	NPC8803
0.7921	Intermediate Similarity	NPC220964
0.7921	Intermediate Similarity	NPC475676
0.7895	Intermediate Similarity	NPC91251
0.7885	Intermediate Similarity	NPC161816
0.7885	Intermediate Similarity	NPC115257
0.7885	Intermediate Similarity	NPC5103
0.7849	Intermediate Similarity	NPC179659
0.7841	Intermediate Similarity	NPC3852
0.7841	Intermediate Similarity	NPC264610
0.783	Intermediate Similarity	NPC469496
0.783	Intermediate Similarity	NPC469463
0.783	Intermediate Similarity	NPC469454
0.7822	Intermediate Similarity	NPC69171
0.7822	Intermediate Similarity	NPC474165
0.7822	Intermediate Similarity	NPC4620
0.7816	Intermediate Similarity	NPC293223
0.781	Intermediate Similarity	NPC475668
0.781	Intermediate Similarity	NPC473921
0.781	Intermediate Similarity	NPC475480
0.7789	Intermediate Similarity	NPC48732
0.7789	Intermediate Similarity	NPC474761
0.7789	Intermediate Similarity	NPC476004
0.7788	Intermediate Similarity	NPC141350
0.7788	Intermediate Similarity	NPC475922
0.7778	Intermediate Similarity	NPC222303
0.7742	Intermediate Similarity	NPC214315
0.7723	Intermediate Similarity	NPC183571
0.7714	Intermediate Similarity	NPC475134
0.7714	Intermediate Similarity	NPC475563
0.7708	Intermediate Similarity	NPC30515
0.7708	Intermediate Similarity	NPC184463
0.7701	Intermediate Similarity	NPC12696
0.7701	Intermediate Similarity	NPC36479
0.77	Intermediate Similarity	NPC167974
0.7692	Intermediate Similarity	NPC233379
0.7692	Intermediate Similarity	NPC474664
0.7692	Intermediate Similarity	NPC14862
0.7685	Intermediate Similarity	NPC474734
0.7685	Intermediate Similarity	NPC470628
0.7685	Intermediate Similarity	NPC474046
0.7685	Intermediate Similarity	NPC259306
0.7684	Intermediate Similarity	NPC246028
0.7684	Intermediate Similarity	NPC307411
0.7677	Intermediate Similarity	NPC473244
0.766	Intermediate Similarity	NPC245004
0.7653	Intermediate Similarity	NPC286612
0.7653	Intermediate Similarity	NPC275310
0.7653	Intermediate Similarity	NPC230347
0.7653	Intermediate Similarity	NPC36954
0.7647	Intermediate Similarity	NPC473694
0.7647	Intermediate Similarity	NPC475334
0.7647	Intermediate Similarity	NPC475623
0.7647	Intermediate Similarity	NPC474775
0.7642	Intermediate Similarity	NPC179798
0.7642	Intermediate Similarity	NPC304180
0.7634	Intermediate Similarity	NPC476725
0.7634	Intermediate Similarity	NPC477746
0.7634	Intermediate Similarity	NPC477747
0.7629	Intermediate Similarity	NPC99653
0.7629	Intermediate Similarity	NPC475912
0.7624	Intermediate Similarity	NPC97435
0.7624	Intermediate Similarity	NPC101067
0.7624	Intermediate Similarity	NPC476134
0.7619	Intermediate Similarity	NPC42662
0.7619	Intermediate Similarity	NPC15218
0.7609	Intermediate Similarity	NPC127917
0.7609	Intermediate Similarity	NPC49208
0.7609	Intermediate Similarity	NPC23748
0.7604	Intermediate Similarity	NPC51004
0.7596	Intermediate Similarity	NPC324327
0.7596	Intermediate Similarity	NPC144854
0.7596	Intermediate Similarity	NPC72813
0.7596	Intermediate Similarity	NPC326994
0.7596	Intermediate Similarity	NPC474421
0.7596	Intermediate Similarity	NPC194620
0.7596	Intermediate Similarity	NPC475176
0.7596	Intermediate Similarity	NPC230541
0.7596	Intermediate Similarity	NPC3316
0.7593	Intermediate Similarity	NPC470919
0.7593	Intermediate Similarity	NPC469877
0.7579	Intermediate Similarity	NPC202672
0.7576	Intermediate Similarity	NPC469528
0.7576	Intermediate Similarity	NPC469369
0.7573	Intermediate Similarity	NPC146731
0.7573	Intermediate Similarity	NPC470104
0.7573	Intermediate Similarity	NPC296950
0.7573	Intermediate Similarity	NPC475335
0.7573	Intermediate Similarity	NPC80809
0.7573	Intermediate Similarity	NPC201144
0.7573	Intermediate Similarity	NPC475331
0.7573	Intermediate Similarity	NPC121518
0.7573	Intermediate Similarity	NPC181104
0.7573	Intermediate Similarity	NPC103298
0.7573	Intermediate Similarity	NPC288502
0.757	Intermediate Similarity	NPC302146
0.7556	Intermediate Similarity	NPC86971
0.7553	Intermediate Similarity	NPC311163
0.7551	Intermediate Similarity	NPC81386
0.7551	Intermediate Similarity	NPC178949
0.7551	Intermediate Similarity	NPC96736
0.7551	Intermediate Similarity	NPC472360
0.7551	Intermediate Similarity	NPC472416
0.7551	Intermediate Similarity	NPC476716
0.7551	Intermediate Similarity	NPC474035
0.7551	Intermediate Similarity	NPC469491
0.7549	Intermediate Similarity	NPC283567
0.7549	Intermediate Similarity	NPC472552
0.7547	Intermediate Similarity	NPC127153
0.7528	Intermediate Similarity	NPC476703
0.7527	Intermediate Similarity	NPC474776
0.7527	Intermediate Similarity	NPC475963
0.7527	Intermediate Similarity	NPC151176
0.7527	Intermediate Similarity	NPC295799
0.7527	Intermediate Similarity	NPC3464
0.7527	Intermediate Similarity	NPC102048
0.7526	Intermediate Similarity	NPC475972
0.7526	Intermediate Similarity	NPC124374
0.7526	Intermediate Similarity	NPC208886
0.7526	Intermediate Similarity	NPC473675
0.7526	Intermediate Similarity	NPC12172
0.7526	Intermediate Similarity	NPC471747
0.7525	Intermediate Similarity	NPC38855
0.7524	Intermediate Similarity	NPC472217
0.7524	Intermediate Similarity	NPC472219
0.7524	Intermediate Similarity	NPC154608
0.7524	Intermediate Similarity	NPC192813
0.7524	Intermediate Similarity	NPC55972
0.7524	Intermediate Similarity	NPC277017
0.7524	Intermediate Similarity	NPC327286
0.7524	Intermediate Similarity	NPC169888
0.7524	Intermediate Similarity	NPC472218
0.7524	Intermediate Similarity	NPC217921
0.7524	Intermediate Similarity	NPC135015
0.7524	Intermediate Similarity	NPC128795
0.7524	Intermediate Similarity	NPC48548
0.7523	Intermediate Similarity	NPC179626
0.75	Intermediate Similarity	NPC20946
0.75	Intermediate Similarity	NPC9303
0.75	Intermediate Similarity	NPC475032
0.75	Intermediate Similarity	NPC475033
0.75	Intermediate Similarity	NPC51978
0.75	Intermediate Similarity	NPC293658
0.75	Intermediate Similarity	NPC60315
0.75	Intermediate Similarity	NPC475802
0.75	Intermediate Similarity	NPC475414
0.75	Intermediate Similarity	NPC98112
0.75	Intermediate Similarity	NPC111348
0.75	Intermediate Similarity	NPC56448
0.75	Intermediate Similarity	NPC470263
0.75	Intermediate Similarity	NPC173172
0.75	Intermediate Similarity	NPC239547
0.75	Intermediate Similarity	NPC473564
0.75	Intermediate Similarity	NPC124246
0.75	Intermediate Similarity	NPC125551
0.75	Intermediate Similarity	NPC309503
0.75	Intermediate Similarity	NPC91197
0.75	Intermediate Similarity	NPC155319
0.75	Intermediate Similarity	NPC133450
0.75	Intermediate Similarity	NPC127609
0.75	Intermediate Similarity	NPC16313
0.75	Intermediate Similarity	NPC474410
0.75	Intermediate Similarity	NPC96597
0.7477	Intermediate Similarity	NPC317107
0.7476	Intermediate Similarity	NPC475321
0.7476	Intermediate Similarity	NPC99266
0.7475	Intermediate Similarity	NPC270013
0.7475	Intermediate Similarity	NPC14961
0.7475	Intermediate Similarity	NPC107476
0.7474	Intermediate Similarity	NPC474765
0.7473	Intermediate Similarity	NPC103634
0.7455	Intermediate Similarity	NPC473590

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 NPC208839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1779
0.2-0.3	3914
0.3-0.4	2328
0.4-0.5	560
0.5-0.6	324
0.6-0.7	83
0.7-0.8	4
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
0.7245	Intermediate Similarity	NPD6698	Approved
0.7245	Intermediate Similarity	NPD46	Approved
0.7172	Intermediate Similarity	NPD7983	Approved
0.7156	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5344	Discontinued
0.7113	Intermediate Similarity	NPD4251	Approved
0.7113	Intermediate Similarity	NPD4250	Approved
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5778	Approved
0.71	Intermediate Similarity	NPD5779	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7019	Intermediate Similarity	NPD7640	Approved
0.7019	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD4249	Approved
0.6939	Remote Similarity	NPD7524	Approved
0.6931	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4821	Approved
0.6881	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD6110	Phase 1
0.6832	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD6084	Phase 2
0.6827	Remote Similarity	NPD6083	Phase 2
0.6804	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD6053	Discontinued
0.6757	Remote Similarity	NPD6371	Approved
0.6702	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD6695	Phase 3
0.6701	Remote Similarity	NPD7154	Phase 3
0.6701	Remote Similarity	NPD5362	Discontinued
0.6699	Remote Similarity	NPD5282	Discontinued
0.6698	Remote Similarity	NPD6648	Approved
0.6697	Remote Similarity	NPD6675	Approved
0.6697	Remote Similarity	NPD7128	Approved
0.6697	Remote Similarity	NPD6402	Approved
0.6697	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6637	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6101	Approved
0.661	Remote Similarity	NPD8517	Approved
0.661	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD8516	Approved
0.661	Remote Similarity	NPD8515	Approved
0.6583	Remote Similarity	NPD7492	Approved
0.6577	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD5737	Approved
0.6535	Remote Similarity	NPD6672	Approved
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD5332	Approved
0.6529	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD6054	Approved
0.6525	Remote Similarity	NPD6059	Approved
0.6518	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD6373	Approved
0.6505	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD7604	Phase 2
0.6495	Remote Similarity	NPD4790	Discontinued
0.6495	Remote Similarity	NPD5369	Approved
0.6486	Remote Similarity	NPD5701	Approved
0.6486	Remote Similarity	NPD5697	Approved
0.6475	Remote Similarity	NPD7078	Approved
0.6475	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD5983	Phase 2
0.6465	Remote Similarity	NPD4786	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD5696	Approved
0.6436	Remote Similarity	NPD7750	Discontinued
0.6429	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD4269	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6423	Remote Similarity	NPD7736	Approved
0.6422	Remote Similarity	NPD7632	Discontinued
0.6417	Remote Similarity	NPD6370	Approved
0.641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6008	Approved
0.6393	Remote Similarity	NPD6336	Discontinued
0.6392	Remote Similarity	NPD6931	Approved
0.6392	Remote Similarity	NPD6930	Phase 2
0.6381	Remote Similarity	NPD7748	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8328	Phase 3
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6355	Remote Similarity	NPD7902	Approved
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD7515	Phase 2
0.6341	Remote Similarity	NPD8074	Phase 3
0.6337	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD6684	Approved
0.6337	Remote Similarity	NPD5330	Approved
0.6337	Remote Similarity	NPD6098	Approved
0.6337	Remote Similarity	NPD7334	Approved
0.6337	Remote Similarity	NPD5786	Approved
0.6337	Remote Similarity	NPD7146	Approved
0.6337	Remote Similarity	NPD6409	Approved
0.6333	Remote Similarity	NPD7503	Approved
0.6333	Remote Similarity	NPD6015	Approved
0.6333	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD6016	Approved
0.6322	Remote Similarity	NPD368	Approved
0.6316	Remote Similarity	NPD6933	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD1695	Approved
0.6311	Remote Similarity	NPD6904	Approved
0.6311	Remote Similarity	NPD6080	Approved
0.6311	Remote Similarity	NPD6673	Approved
0.6311	Remote Similarity	NPD6051	Approved
0.6303	Remote Similarity	NPD7516	Approved
0.63	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8133	Approved
0.6289	Remote Similarity	NPD6929	Approved
0.6281	Remote Similarity	NPD5988	Approved
0.6275	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5211	Phase 2
0.6262	Remote Similarity	NPD7839	Suspended
0.626	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6238	Remote Similarity	NPD1696	Phase 3
0.6238	Remote Similarity	NPD5363	Approved
0.6224	Remote Similarity	NPD5368	Approved
0.6224	Remote Similarity	NPD7525	Registered
0.6224	Remote Similarity	NPD4252	Approved
0.6214	Remote Similarity	NPD6903	Approved
0.6214	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7339	Approved
0.6211	Remote Similarity	NPD6942	Approved
0.6204	Remote Similarity	NPD4755	Approved
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD7087	Discontinued
0.619	Remote Similarity	NPD6050	Approved
0.618	Remote Similarity	NPD3197	Phase 1
0.6176	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5141	Approved
0.616	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7260	Phase 2
0.6139	Remote Similarity	NPD3665	Phase 1
0.6139	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD7319	Approved
0.6105	Remote Similarity	NPD6926	Approved
0.6105	Remote Similarity	NPD6924	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5692	Phase 3
0.6095	Remote Similarity	NPD5785	Approved
0.6095	Remote Similarity	NPD3168	Discontinued
0.6091	Remote Similarity	NPD4700	Approved
0.6091	Remote Similarity	NPD4696	Approved
0.6091	Remote Similarity	NPD5285	Approved
0.6091	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD6335	Approved
0.6082	Remote Similarity	NPD6925	Approved
0.6082	Remote Similarity	NPD5776	Phase 2
0.6078	Remote Similarity	NPD6893	Approved
0.6078	Remote Similarity	NPD5329	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