NPASS Compound

Structure

CID309656 OpenBabel06191716122D 29 31 0 0 1 0 0 0 0 0999 V2000 -2.5000 -3.5981 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 3.2709 -2.5000 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 -0.6923 1.8035 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 -1.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 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 2.4049 -2.0000 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 2.4049 -1.0000 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 -0.9511 0.3090 0.0000 C 0 0 1 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 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 -0.5878 0.8090 0.0000 C 0 0 2 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 -1.9021 0.6180 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 -1.5013 1.2158 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 14 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 16 14 1 6 0 0 0 16 21 1 0 0 0 0 17 13 1 6 0 0 0 17 20 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 6 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 15 1 1 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.29
Volume:	436.669
LogP:	4.371
LogD:	3.956
LogS:	-3.582
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	5.961
Fsp3:	0.875
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:	-4.634
MDCK Permeability:	4.628360693459399e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.146
30% Bioavailability (F30%):	0.248

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	95.4802474975586%
Volume Distribution (VD):	1.642
Pgp-substrate:	3.3707213401794434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	10.155
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.504
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.092
Carcinogencity:	0.044
Eye Corrosion:	0.013
Eye Irritation:	0.03
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC309656

Natural Product ID:	NPC309656
*Common Name:**	Hirsutalin E
IUPAC Name:	n.a.
Synonyms:	Hirsutalin E
Standard InCHIKey:	AOODOWQDWVZWQC-QGLKYHSXSA-N
Standard InCHI:	InChI=1S/C24H40O5/c1-7-8-19(26)29-24(6)12-11-18(25)23(5,27)13-17-20-15(4)9-10-16(14(2)3)21(20)22(24)28-17/h9,14,16-18,20-22,25,27H,7-8,10-13H2,1-6H3/t16-,17-,18+,20-,21-,22-,23+,24-/m1/s1
SMILES:	CCCC(=O)O[C@]1(C)CC[C@H](O)[C@@](C[C@H]2O[C@@H]1[C@@H]1[C@H](CC=C([C@H]21)C)C(C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631451
PubChem CID:	50900138
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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	41000.0	nM	PMID[546624]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35000.0	nM	PMID[546624]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	34000.0	nM	PMID[546624]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	34000.0	nM	PMID[546624]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4700.0	nM	PMID[546624]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14000.0	nM	PMID[546624]

☑ 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 NPC309656 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	173
0.1-0.2	1125
0.2-0.3	5054
0.3-0.4	14023
0.4-0.5	9653
0.5-0.6	7923
0.6-0.7	4259
0.7-0.8	470
0.8-0.85	13
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	NPC208839
0.9157	High Similarity	NPC239308
0.8916	High Similarity	NPC118116
0.8636	High Similarity	NPC92370
0.8539	High Similarity	NPC291875
0.8506	High Similarity	NPC196911
0.8506	High Similarity	NPC471379
0.8471	Intermediate Similarity	NPC77003
0.8444	Intermediate Similarity	NPC312471
0.8444	Intermediate Similarity	NPC471378
0.8409	Intermediate Similarity	NPC322922
0.8409	Intermediate Similarity	NPC475684
0.8409	Intermediate Similarity	NPC321812
0.8387	Intermediate Similarity	NPC8803
0.8372	Intermediate Similarity	NPC103171
0.8352	Intermediate Similarity	NPC312805
0.8352	Intermediate Similarity	NPC122057
0.8316	Intermediate Similarity	NPC272223
0.8315	Intermediate Similarity	NPC44538
0.8313	Intermediate Similarity	NPC293223
0.8276	Intermediate Similarity	NPC5958
0.8222	Intermediate Similarity	NPC476723
0.8222	Intermediate Similarity	NPC75443
0.8222	Intermediate Similarity	NPC470260
0.8222	Intermediate Similarity	NPC476724
0.8202	Intermediate Similarity	NPC214315
0.8193	Intermediate Similarity	NPC36479
0.8132	Intermediate Similarity	NPC161560
0.8125	Intermediate Similarity	NPC167974
0.8118	Intermediate Similarity	NPC3852
0.809	Intermediate Similarity	NPC477747
0.809	Intermediate Similarity	NPC477746
0.8085	Intermediate Similarity	NPC476720
0.8085	Intermediate Similarity	NPC230347
0.8085	Intermediate Similarity	NPC275310
0.8085	Intermediate Similarity	NPC286612
0.8061	Intermediate Similarity	NPC474165
0.8061	Intermediate Similarity	NPC69171
0.8041	Intermediate Similarity	NPC101067
0.8041	Intermediate Similarity	NPC476134
0.8021	Intermediate Similarity	NPC222303
0.8	Intermediate Similarity	NPC40049
0.7979	Intermediate Similarity	NPC178949
0.7979	Intermediate Similarity	NPC96736
0.7979	Intermediate Similarity	NPC476716
0.7976	Intermediate Similarity	NPC12696
0.7959	Intermediate Similarity	NPC283567
0.7959	Intermediate Similarity	NPC183571
0.7957	Intermediate Similarity	NPC91251
0.7957	Intermediate Similarity	NPC184463
0.7941	Intermediate Similarity	NPC127153
0.7917	Intermediate Similarity	NPC111348
0.7917	Intermediate Similarity	NPC124246
0.7907	Intermediate Similarity	NPC191345
0.7907	Intermediate Similarity	NPC264610
0.7907	Intermediate Similarity	NPC252483
0.7889	Intermediate Similarity	NPC329738
0.7889	Intermediate Similarity	NPC476725
0.7882	Intermediate Similarity	NPC329626
0.7872	Intermediate Similarity	NPC477615
0.7865	Intermediate Similarity	NPC127917
0.7857	Intermediate Similarity	NPC476132
0.7849	Intermediate Similarity	NPC48732
0.7835	Intermediate Similarity	NPC241657
0.7822	Intermediate Similarity	NPC293512
0.7822	Intermediate Similarity	NPC59530
0.78	Intermediate Similarity	NPC258532
0.7778	Intermediate Similarity	NPC472552
0.7778	Intermediate Similarity	NPC476126
0.7778	Intermediate Similarity	NPC476235
0.7766	Intermediate Similarity	NPC30515
0.7755	Intermediate Similarity	NPC476195
0.7745	Intermediate Similarity	NPC128795
0.7745	Intermediate Similarity	NPC48548
0.7745	Intermediate Similarity	NPC217921
0.7745	Intermediate Similarity	NPC135015
0.7742	Intermediate Similarity	NPC133450
0.7742	Intermediate Similarity	NPC473564
0.7742	Intermediate Similarity	NPC307411
0.7738	Intermediate Similarity	NPC476709
0.7732	Intermediate Similarity	NPC125551
0.7732	Intermediate Similarity	NPC309503
0.7732	Intermediate Similarity	NPC239547
0.7732	Intermediate Similarity	NPC155319
0.7732	Intermediate Similarity	NPC96597
0.7732	Intermediate Similarity	NPC473244
0.7732	Intermediate Similarity	NPC475033
0.7732	Intermediate Similarity	NPC91197
0.7732	Intermediate Similarity	NPC475032
0.7727	Intermediate Similarity	NPC103634
0.7708	Intermediate Similarity	NPC36954
0.77	Intermediate Similarity	NPC475334
0.77	Intermediate Similarity	NPC475623
0.77	Intermediate Similarity	NPC4620
0.77	Intermediate Similarity	NPC474775
0.77	Intermediate Similarity	NPC475321
0.77	Intermediate Similarity	NPC473694
0.7684	Intermediate Similarity	NPC99653
0.7684	Intermediate Similarity	NPC475912
0.7684	Intermediate Similarity	NPC476300
0.7684	Intermediate Similarity	NPC212486
0.7677	Intermediate Similarity	NPC475617
0.7677	Intermediate Similarity	NPC476246
0.7677	Intermediate Similarity	NPC472554
0.7677	Intermediate Similarity	NPC477870
0.7677	Intermediate Similarity	NPC477871
0.7677	Intermediate Similarity	NPC476213
0.7674	Intermediate Similarity	NPC136424
0.767	Intermediate Similarity	NPC316974
0.767	Intermediate Similarity	NPC40728
0.767	Intermediate Similarity	NPC475922
0.7667	Intermediate Similarity	NPC23748
0.7667	Intermediate Similarity	NPC49208
0.7667	Intermediate Similarity	NPC231601
0.766	Intermediate Similarity	NPC51004
0.766	Intermediate Similarity	NPC177668
0.766	Intermediate Similarity	NPC474761
0.766	Intermediate Similarity	NPC478003
0.766	Intermediate Similarity	NPC158388
0.766	Intermediate Similarity	NPC159876
0.766	Intermediate Similarity	NPC476004
0.766	Intermediate Similarity	NPC478004
0.7653	Intermediate Similarity	NPC470066
0.7653	Intermediate Similarity	NPC477876
0.7653	Intermediate Similarity	NPC477875
0.7653	Intermediate Similarity	NPC470067
0.7653	Intermediate Similarity	NPC470068
0.7647	Intermediate Similarity	NPC88013
0.7647	Intermediate Similarity	NPC125423
0.764	Intermediate Similarity	NPC211049
0.7634	Intermediate Similarity	NPC202672
0.7629	Intermediate Similarity	NPC469528
0.7629	Intermediate Similarity	NPC469369
0.7624	Intermediate Similarity	NPC103298
0.7624	Intermediate Similarity	NPC474550
0.7624	Intermediate Similarity	NPC288502
0.7624	Intermediate Similarity	NPC121518
0.7624	Intermediate Similarity	NPC80809
0.7624	Intermediate Similarity	NPC475335
0.7624	Intermediate Similarity	NPC475331
0.7624	Intermediate Similarity	NPC121566
0.7624	Intermediate Similarity	NPC473577
0.7624	Intermediate Similarity	NPC100955
0.7624	Intermediate Similarity	NPC296950
0.7624	Intermediate Similarity	NPC146731
0.7624	Intermediate Similarity	NPC201144
0.7624	Intermediate Similarity	NPC181104
0.7624	Intermediate Similarity	NPC471293
0.7624	Intermediate Similarity	NPC475585
0.7624	Intermediate Similarity	NPC470104
0.7624	Intermediate Similarity	NPC85593
0.7624	Intermediate Similarity	NPC475676
0.7624	Intermediate Similarity	NPC31430
0.7624	Intermediate Similarity	NPC220964
0.7614	Intermediate Similarity	NPC476701
0.76	Intermediate Similarity	NPC238397
0.76	Intermediate Similarity	NPC154452
0.76	Intermediate Similarity	NPC200672
0.76	Intermediate Similarity	NPC471363
0.76	Intermediate Similarity	NPC214714
0.7596	Intermediate Similarity	NPC161816
0.7596	Intermediate Similarity	NPC115257
0.7596	Intermediate Similarity	NPC101450
0.7596	Intermediate Similarity	NPC5103
0.7586	Intermediate Similarity	NPC476703
0.7582	Intermediate Similarity	NPC474776
0.7582	Intermediate Similarity	NPC295799
0.7579	Intermediate Similarity	NPC124374
0.7579	Intermediate Similarity	NPC208886
0.7579	Intermediate Similarity	NPC12172
0.7579	Intermediate Similarity	NPC165180
0.7579	Intermediate Similarity	NPC475972
0.7576	Intermediate Similarity	NPC38855
0.7576	Intermediate Similarity	NPC188968
0.7573	Intermediate Similarity	NPC258323
0.7573	Intermediate Similarity	NPC472218
0.7573	Intermediate Similarity	NPC472217
0.7573	Intermediate Similarity	NPC311223
0.7573	Intermediate Similarity	NPC295389
0.7573	Intermediate Similarity	NPC472219
0.757	Intermediate Similarity	NPC189126
0.7558	Intermediate Similarity	NPC93213
0.7553	Intermediate Similarity	NPC261320
0.7553	Intermediate Similarity	NPC246028
0.7553	Intermediate Similarity	NPC473058
0.7549	Intermediate Similarity	NPC60315
0.7549	Intermediate Similarity	NPC475290
0.7549	Intermediate Similarity	NPC470980
0.7549	Intermediate Similarity	NPC95243
0.7549	Intermediate Similarity	NPC102352
0.7549	Intermediate Similarity	NPC472655
0.7549	Intermediate Similarity	NPC63023
0.7549	Intermediate Similarity	NPC470263
0.7549	Intermediate Similarity	NPC477877
0.7547	Intermediate Similarity	NPC469454
0.7547	Intermediate Similarity	NPC474410
0.7547	Intermediate Similarity	NPC293658
0.7547	Intermediate Similarity	NPC469496
0.7547	Intermediate Similarity	NPC469463
0.7528	Intermediate Similarity	NPC100697

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 NPC309656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1794
0.2-0.3	3932
0.3-0.4	2264
0.4-0.5	576
0.5-0.6	333
0.6-0.7	83
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
0.7474	Intermediate Similarity	NPD6698	Approved
0.7474	Intermediate Similarity	NPD46	Approved
0.7292	Intermediate Similarity	NPD7838	Discovery
0.7216	Intermediate Similarity	NPD7983	Approved
0.7158	Intermediate Similarity	NPD4250	Approved
0.7158	Intermediate Similarity	NPD4251	Approved
0.7157	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7129	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD6686	Approved
0.7053	Intermediate Similarity	NPD4249	Approved
0.701	Intermediate Similarity	NPD6101	Approved
0.701	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7524	Approved
0.6972	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD7638	Approved
0.6957	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4821	Approved
0.6957	Remote Similarity	NPD4820	Approved
0.6957	Remote Similarity	NPD4819	Approved
0.6957	Remote Similarity	NPD4822	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6881	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6084	Phase 2
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6435	Approved
0.6796	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6371	Approved
0.6757	Remote Similarity	NPD4632	Approved
0.6739	Remote Similarity	NPD4271	Approved
0.6739	Remote Similarity	NPD4268	Approved
0.6737	Remote Similarity	NPD7154	Phase 3
0.6737	Remote Similarity	NPD6695	Phase 3
0.6733	Remote Similarity	NPD5282	Discontinued
0.6731	Remote Similarity	NPD6648	Approved
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6702	Remote Similarity	NPD5369	Approved
0.6697	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4786	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6632	Remote Similarity	NPD3667	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.6598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5368	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD6008	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD7515	Phase 2
0.6531	Remote Similarity	NPD7334	Approved
0.6531	Remote Similarity	NPD7521	Approved
0.6531	Remote Similarity	NPD6684	Approved
0.6531	Remote Similarity	NPD5330	Approved
0.6531	Remote Similarity	NPD6409	Approved
0.6531	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD7327	Approved
0.6522	Remote Similarity	NPD7328	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6514	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD1695	Approved
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD7503	Approved
0.6496	Remote Similarity	NPD8033	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6486	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6466	Remote Similarity	NPD7516	Approved
0.6465	Remote Similarity	NPD7750	Discontinued
0.646	Remote Similarity	NPD8133	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7736	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6436	Remote Similarity	NPD3168	Discontinued
0.6435	Remote Similarity	NPD6009	Approved
0.6435	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6421	Remote Similarity	NPD6930	Phase 2
0.6421	Remote Similarity	NPD7525	Registered
0.6421	Remote Similarity	NPD6931	Approved
0.6417	Remote Similarity	NPD7507	Approved
0.6413	Remote Similarity	NPD7339	Approved
0.6413	Remote Similarity	NPD6942	Approved
0.641	Remote Similarity	NPD8294	Approved
0.641	Remote Similarity	NPD8377	Approved
0.64	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6903	Approved
0.64	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD6672	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6392	Remote Similarity	NPD5331	Approved
0.6392	Remote Similarity	NPD6110	Phase 1
0.6392	Remote Similarity	NPD5332	Approved
0.6387	Remote Similarity	NPD7604	Phase 2
0.6387	Remote Similarity	NPD8328	Phase 3
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD8074	Phase 3
0.6356	Remote Similarity	NPD8378	Approved
0.6356	Remote Similarity	NPD5983	Phase 2
0.6356	Remote Similarity	NPD8380	Approved
0.6356	Remote Similarity	NPD8335	Approved
0.6356	Remote Similarity	NPD6015	Approved
0.6356	Remote Similarity	NPD8379	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6356	Remote Similarity	NPD8296	Approved
0.6354	Remote Similarity	NPD4790	Discontinued
0.6346	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6051	Approved
0.6337	Remote Similarity	NPD4753	Phase 2
0.6327	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD3133	Approved
0.6327	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD6929	Approved
0.6316	Remote Similarity	NPD7645	Phase 2
0.6306	Remote Similarity	NPD6011	Approved
0.6304	Remote Similarity	NPD6926	Approved
0.6304	Remote Similarity	NPD6924	Approved
0.6303	Remote Similarity	NPD5988	Approved
0.6296	Remote Similarity	NPD7632	Discontinued
0.6289	Remote Similarity	NPD4270	Approved
0.6289	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD7839	Suspended
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6336	Discontinued
0.6277	Remote Similarity	NPD6932	Approved
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD4755	Approved
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6685	Approved
0.6214	Remote Similarity	NPD8035	Phase 2
0.6214	Remote Similarity	NPD8034	Phase 2
0.6214	Remote Similarity	NPD7087	Discontinued
0.6214	Remote Similarity	NPD5284	Approved
0.6214	Remote Similarity	NPD5281	Approved
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD6098	Approved
0.62	Remote Similarity	NPD5786	Approved
0.6195	Remote Similarity	NPD4634	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6080	Approved
0.6176	Remote Similarity	NPD6904	Approved
0.6176	Remote Similarity	NPD6673	Approved
0.6176	Remote Similarity	NPD5328	Approved
0.6163	Remote Similarity	NPD368	Approved
0.6162	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD4202	Approved
0.6147	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6683	Phase 2
0.6139	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6067	Discontinued
0.6111	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6105	Remote Similarity	NPD5776	Phase 2

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