NPASS Compound

Structure

NPC272899 OpenBabel07101719522D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 20 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	2.784
LogD:	2.541
LogS:	-2.84
# Rotatable Bonds:	2
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.875
Synthetic Accessibility Score:	4.664
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.599
MDCK Permeability:	1.3604848390968982e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.689
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	94.61026763916016%
Volume Distribution (VD):	1.488
Pgp-substrate:	3.226551055908203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.551
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	11.941
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.6
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.341
Skin Sensitization:	0.756
Carcinogencity:	0.971
Eye Corrosion:	0.004
Eye Irritation:	0.093
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC272899

Natural Product ID:	NPC272899
*Common Name:**	19,20-Dihydroxyspongia-13(16),14-Diene
IUPAC Name:	[(3bR,5aS,6S,9aS,9bS)-9a-(hydroxymethyl)-3b,6-dimethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[2,1-e][2]benzofuran-6-yl]methanol
Synonyms:
Standard InCHIKey:	HJTMHDSGDBNZJV-UHZRXMQZSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-18(12-21)7-3-8-20(13-22)16(18)6-9-19(2)15-11-23-10-14(15)4-5-17(19)20/h10-11,16-17,21-22H,3-9,12-13H2,1-2H3/t16-,17-,18+,19-,20+/m0/s1
SMILES:	OC[C@]12CCC[C@]([C@@H]1CC[C@@]1([C@@H]2CCc2c1coc2)C)(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512451
PubChem CID:	24878745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane 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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3511	Individual Protein	Thyrotropin-releasing hormone receptor 2	Rattus norvegicus	IC50	=	600000.0	nM	PMID[497604]

☑ 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 NPC272899 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	229
0.1-0.2	1250
0.2-0.3	2716
0.3-0.4	6439
0.4-0.5	12794
0.5-0.6	13205
0.6-0.7	5407
0.7-0.8	529
0.8-0.85	84
0.85-0.9	30
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC303010
0.9576	High Similarity	NPC130275
0.9504	High Similarity	NPC223063
0.9504	High Similarity	NPC120836
0.9478	High Similarity	NPC212918
0.9244	High Similarity	NPC36255
0.9174	High Similarity	NPC230979
0.912	High Similarity	NPC471995
0.9098	High Similarity	NPC23086
0.9091	High Similarity	NPC83115
0.8943	High Similarity	NPC138139
0.8943	High Similarity	NPC46536
0.8915	High Similarity	NPC4764
0.8889	High Similarity	NPC89133
0.8828	High Similarity	NPC471998
0.881	High Similarity	NPC476925
0.88	High Similarity	NPC329707
0.88	High Similarity	NPC207294
0.88	High Similarity	NPC112706
0.88	High Similarity	NPC476917
0.88	High Similarity	NPC327527
0.877	High Similarity	NPC477967
0.874	High Similarity	NPC61788
0.873	High Similarity	NPC198904
0.872	High Similarity	NPC83178
0.8702	High Similarity	NPC471996
0.8699	High Similarity	NPC16922
0.8651	High Similarity	NPC477040
0.864	High Similarity	NPC74612
0.8615	High Similarity	NPC476947
0.8605	High Similarity	NPC218838
0.8582	High Similarity	NPC20578
0.8582	High Similarity	NPC62103
0.856	High Similarity	NPC179354
0.855	High Similarity	NPC46896
0.8537	High Similarity	NPC97566
0.8504	High Similarity	NPC477123
0.8504	High Similarity	NPC477966
0.85	High Similarity	NPC150895
0.8496	Intermediate Similarity	NPC202260
0.848	Intermediate Similarity	NPC178382
0.8473	Intermediate Similarity	NPC158525
0.8444	Intermediate Similarity	NPC263337
0.8433	Intermediate Similarity	NPC67003
0.8425	Intermediate Similarity	NPC290955
0.8409	Intermediate Similarity	NPC214572
0.8394	Intermediate Similarity	NPC41182
0.8382	Intermediate Similarity	NPC103134
0.8359	Intermediate Similarity	NPC477039
0.8358	Intermediate Similarity	NPC90953
0.8346	Intermediate Similarity	NPC310043
0.8293	Intermediate Similarity	NPC243704
0.8281	Intermediate Similarity	NPC246392
0.8273	Intermediate Similarity	NPC216755
0.8248	Intermediate Similarity	NPC243577
0.8235	Intermediate Similarity	NPC205765
0.8217	Intermediate Similarity	NPC26532
0.8214	Intermediate Similarity	NPC471007
0.8209	Intermediate Similarity	NPC307401
0.8189	Intermediate Similarity	NPC477965
0.8189	Intermediate Similarity	NPC243269
0.8189	Intermediate Similarity	NPC477038
0.8188	Intermediate Similarity	NPC476944
0.8182	Intermediate Similarity	NPC471006
0.8175	Intermediate Similarity	NPC317217
0.8175	Intermediate Similarity	NPC52412
0.8175	Intermediate Similarity	NPC121158
0.8143	Intermediate Similarity	NPC471174
0.8129	Intermediate Similarity	NPC5676
0.8129	Intermediate Similarity	NPC185456
0.8125	Intermediate Similarity	NPC300098
0.8125	Intermediate Similarity	NPC290193
0.8116	Intermediate Similarity	NPC476946
0.8116	Intermediate Similarity	NPC64568
0.8106	Intermediate Similarity	NPC473982
0.8077	Intermediate Similarity	NPC279877
0.8065	Intermediate Similarity	NPC208906
0.8065	Intermediate Similarity	NPC144745
0.8058	Intermediate Similarity	NPC251865
0.8045	Intermediate Similarity	NPC293253
0.803	Intermediate Similarity	NPC298190
0.8029	Intermediate Similarity	NPC90296
0.8029	Intermediate Similarity	NPC148374
0.8015	Intermediate Similarity	NPC59502
0.8015	Intermediate Similarity	NPC476943
0.8014	Intermediate Similarity	NPC302987
0.8014	Intermediate Similarity	NPC250228
0.7986	Intermediate Similarity	NPC294511
0.7986	Intermediate Similarity	NPC121615
0.7986	Intermediate Similarity	NPC267632
0.7986	Intermediate Similarity	NPC472672
0.7984	Intermediate Similarity	NPC59035
0.7984	Intermediate Similarity	NPC79202
0.7972	Intermediate Similarity	NPC228842
0.7972	Intermediate Similarity	NPC196846
0.7972	Intermediate Similarity	NPC212257
0.7958	Intermediate Similarity	NPC476941
0.7958	Intermediate Similarity	NPC476942
0.7943	Intermediate Similarity	NPC97904
0.7941	Intermediate Similarity	NPC42400
0.7941	Intermediate Similarity	NPC310830
0.7931	Intermediate Similarity	NPC253201
0.7931	Intermediate Similarity	NPC34421
0.7931	Intermediate Similarity	NPC98206
0.7931	Intermediate Similarity	NPC237259
0.7931	Intermediate Similarity	NPC302054
0.7907	Intermediate Similarity	NPC118853
0.7902	Intermediate Similarity	NPC69647
0.7902	Intermediate Similarity	NPC234494
0.7902	Intermediate Similarity	NPC472654
0.7902	Intermediate Similarity	NPC125182
0.7902	Intermediate Similarity	NPC470998
0.7902	Intermediate Similarity	NPC195325
0.7899	Intermediate Similarity	NPC56197
0.7887	Intermediate Similarity	NPC476937
0.7887	Intermediate Similarity	NPC255414
0.7887	Intermediate Similarity	NPC476938
0.7868	Intermediate Similarity	NPC146872
0.7862	Intermediate Similarity	NPC470996
0.7862	Intermediate Similarity	NPC469503
0.7857	Intermediate Similarity	NPC87466
0.7851	Intermediate Similarity	NPC177331
0.7847	Intermediate Similarity	NPC470997
0.7846	Intermediate Similarity	NPC471074
0.7846	Intermediate Similarity	NPC473885
0.7817	Intermediate Similarity	NPC346
0.7808	Intermediate Similarity	NPC178932
0.7794	Intermediate Similarity	NPC92941
0.7793	Intermediate Similarity	NPC272590
0.7778	Intermediate Similarity	NPC214097
0.7778	Intermediate Similarity	NPC470740
0.7778	Intermediate Similarity	NPC211625
0.777	Intermediate Similarity	NPC18904
0.777	Intermediate Similarity	NPC304692
0.777	Intermediate Similarity	NPC194499
0.7762	Intermediate Similarity	NPC71821
0.7755	Intermediate Similarity	NPC155939
0.7755	Intermediate Similarity	NPC92979
0.7755	Intermediate Similarity	NPC35000
0.7755	Intermediate Similarity	NPC141538
0.7755	Intermediate Similarity	NPC469336
0.7755	Intermediate Similarity	NPC296807
0.7754	Intermediate Similarity	NPC220094
0.7754	Intermediate Similarity	NPC472376
0.7752	Intermediate Similarity	NPC471549
0.7752	Intermediate Similarity	NPC473379
0.7744	Intermediate Similarity	NPC208389
0.774	Intermediate Similarity	NPC145830
0.774	Intermediate Similarity	NPC33938
0.774	Intermediate Similarity	NPC75906
0.774	Intermediate Similarity	NPC246164
0.774	Intermediate Similarity	NPC475777
0.7724	Intermediate Similarity	NPC277525
0.7718	Intermediate Similarity	NPC472823
0.7718	Intermediate Similarity	NPC474611
0.771	Intermediate Similarity	NPC474829
0.7708	Intermediate Similarity	NPC93666
0.7704	Intermediate Similarity	NPC471817
0.7703	Intermediate Similarity	NPC104736
0.7703	Intermediate Similarity	NPC41880
0.7692	Intermediate Similarity	NPC470999
0.7687	Intermediate Similarity	NPC282445
0.7687	Intermediate Similarity	NPC30222
0.7687	Intermediate Similarity	NPC57998
0.7687	Intermediate Similarity	NPC114880
0.7687	Intermediate Similarity	NPC44606
0.7681	Intermediate Similarity	NPC470742
0.7676	Intermediate Similarity	NPC199044
0.7676	Intermediate Similarity	NPC158871
0.7676	Intermediate Similarity	NPC142113
0.7676	Intermediate Similarity	NPC238843
0.7674	Intermediate Similarity	NPC79557
0.7671	Intermediate Similarity	NPC472787
0.7667	Intermediate Similarity	NPC335761
0.766	Intermediate Similarity	NPC473152
0.7651	Intermediate Similarity	NPC88007
0.7651	Intermediate Similarity	NPC7059
0.7651	Intermediate Similarity	NPC472772
0.7651	Intermediate Similarity	NPC195954
0.7643	Intermediate Similarity	NPC473983
0.7643	Intermediate Similarity	NPC201370
0.7635	Intermediate Similarity	NPC281258
0.7635	Intermediate Similarity	NPC179170
0.7635	Intermediate Similarity	NPC75310
0.7635	Intermediate Similarity	NPC472785
0.7635	Intermediate Similarity	NPC88958
0.7626	Intermediate Similarity	NPC236532
0.7622	Intermediate Similarity	NPC290038
0.7622	Intermediate Similarity	NPC245522
0.7622	Intermediate Similarity	NPC114513
0.7619	Intermediate Similarity	NPC476940
0.7619	Intermediate Similarity	NPC476939
0.7619	Intermediate Similarity	NPC28054
0.7619	Intermediate Similarity	NPC268905
0.7616	Intermediate Similarity	NPC18986
0.7616	Intermediate Similarity	NPC470792
0.7616	Intermediate Similarity	NPC79571
0.7616	Intermediate Similarity	NPC263432
0.7606	Intermediate Similarity	NPC205071
0.76	Intermediate Similarity	NPC140952

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 NPC272899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	933
0.2-0.3	1812
0.3-0.4	2821
0.4-0.5	2154
0.5-0.6	1030
0.6-0.7	168
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
0.7877	Intermediate Similarity	NPD5761	Phase 2
0.7877	Intermediate Similarity	NPD5760	Phase 2
0.7571	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6273	Approved
0.7172	Intermediate Similarity	NPD4628	Phase 3
0.7068	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7003	Approved
0.7021	Intermediate Similarity	NPD4140	Approved
0.7013	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8032	Phase 2
0.6933	Remote Similarity	NPD6765	Approved
0.6933	Remote Similarity	NPD6764	Approved
0.6929	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3972	Approved
0.6908	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5735	Approved
0.6849	Remote Similarity	NPD2344	Approved
0.6849	Remote Similarity	NPD2346	Discontinued
0.6835	Remote Similarity	NPD2798	Approved
0.6828	Remote Similarity	NPD2799	Discontinued
0.6826	Remote Similarity	NPD8434	Phase 2
0.6812	Remote Similarity	NPD1876	Approved
0.6788	Remote Similarity	NPD1608	Approved
0.6781	Remote Similarity	NPD6099	Approved
0.6781	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6785	Approved
0.6766	Remote Similarity	NPD6784	Approved
0.6761	Remote Similarity	NPD2313	Discontinued
0.6739	Remote Similarity	NPD5327	Phase 3
0.6735	Remote Similarity	NPD1471	Phase 3
0.6715	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1283	Approved
0.6688	Remote Similarity	NPD7458	Discontinued
0.6687	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6644	Remote Similarity	NPD2800	Approved
0.6643	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD3764	Approved
0.6622	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6002	Phase 3
0.6622	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6005	Phase 3
0.6622	Remote Similarity	NPD6004	Phase 3
0.6621	Remote Similarity	NPD6355	Discontinued
0.6618	Remote Similarity	NPD5585	Approved
0.6617	Remote Similarity	NPD5951	Approved
0.66	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4110	Phase 3
0.6599	Remote Similarity	NPD4308	Phase 3
0.6582	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3226	Approved
0.6575	Remote Similarity	NPD6353	Approved
0.6573	Remote Similarity	NPD7008	Discontinued
0.6569	Remote Similarity	NPD1778	Approved
0.6569	Remote Similarity	NPD3019	Approved
0.6569	Remote Similarity	NPD17	Approved
0.6554	Remote Similarity	NPD4477	Approved
0.6554	Remote Similarity	NPD2796	Approved
0.6554	Remote Similarity	NPD4476	Approved
0.6554	Remote Similarity	NPD1551	Phase 2
0.6544	Remote Similarity	NPD1894	Discontinued
0.6536	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2532	Approved
0.6536	Remote Similarity	NPD2533	Approved
0.6536	Remote Similarity	NPD2534	Approved
0.6528	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6798	Discontinued
0.6527	Remote Similarity	NPD6559	Discontinued
0.6519	Remote Similarity	NPD7819	Suspended
0.6503	Remote Similarity	NPD6832	Phase 2
0.6496	Remote Similarity	NPD1651	Approved
0.649	Remote Similarity	NPD3750	Approved
0.6483	Remote Similarity	NPD6663	Approved
0.6479	Remote Similarity	NPD4624	Approved
0.6475	Remote Similarity	NPD1281	Approved
0.6458	Remote Similarity	NPD7095	Approved
0.6449	Remote Similarity	NPD2932	Approved
0.6444	Remote Similarity	NPD7157	Approved
0.6439	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4307	Phase 2
0.6438	Remote Similarity	NPD2979	Phase 3
0.6438	Remote Similarity	NPD3620	Phase 2
0.6438	Remote Similarity	NPD7768	Phase 2
0.6438	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5736	Approved
0.6433	Remote Similarity	NPD6599	Discontinued
0.6433	Remote Similarity	NPD7028	Phase 2
0.6429	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3267	Approved
0.6408	Remote Similarity	NPD3266	Approved
0.6405	Remote Similarity	NPD7236	Approved
0.6405	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5763	Approved
0.64	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5762	Approved
0.64	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3749	Approved
0.6392	Remote Similarity	NPD7411	Suspended
0.6383	Remote Similarity	NPD4359	Approved
0.6382	Remote Similarity	NPD8166	Discontinued
0.638	Remote Similarity	NPD6959	Discontinued
0.6376	Remote Similarity	NPD3748	Approved
0.6376	Remote Similarity	NPD7033	Discontinued
0.637	Remote Similarity	NPD6233	Phase 2
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1549	Phase 2
0.6358	Remote Similarity	NPD4534	Discontinued
0.6357	Remote Similarity	NPD1201	Approved
0.6352	Remote Similarity	NPD7577	Discontinued
0.6352	Remote Similarity	NPD37	Approved
0.6351	Remote Similarity	NPD6651	Approved
0.6347	Remote Similarity	NPD5844	Phase 1
0.6346	Remote Similarity	NPD7427	Discontinued
0.6346	Remote Similarity	NPD3869	Phase 3
0.6346	Remote Similarity	NPD3873	Phase 3
0.6346	Remote Similarity	NPD920	Approved
0.6338	Remote Similarity	NPD6696	Suspended
0.6335	Remote Similarity	NPD4967	Phase 2
0.6335	Remote Similarity	NPD4966	Approved
0.6335	Remote Similarity	NPD4965	Approved
0.6333	Remote Similarity	NPD2935	Discontinued
0.6331	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1243	Approved
0.6312	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD9717	Approved
0.6312	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7440	Discontinued
0.6294	Remote Similarity	NPD1203	Approved
0.6294	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6677	Suspended
0.6288	Remote Similarity	NPD2684	Approved
0.6287	Remote Similarity	NPD7177	Discontinued
0.6286	Remote Similarity	NPD3023	Approved
0.6286	Remote Similarity	NPD3026	Approved
0.6284	Remote Similarity	NPD4622	Approved
0.6284	Remote Similarity	NPD4618	Approved
0.6276	Remote Similarity	NPD2614	Approved
0.6276	Remote Similarity	NPD4908	Phase 1
0.6269	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1510	Phase 2
0.6266	Remote Similarity	NPD2651	Approved
0.6266	Remote Similarity	NPD2649	Approved
0.6259	Remote Similarity	NPD5691	Approved
0.6259	Remote Similarity	NPD3025	Approved
0.6259	Remote Similarity	NPD3024	Approved
0.625	Remote Similarity	NPD2629	Approved
0.625	Remote Similarity	NPD970	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6280	Approved
0.625	Remote Similarity	NPD5958	Discontinued
0.625	Remote Similarity	NPD5647	Approved
0.625	Remote Similarity	NPD6279	Approved
0.6242	Remote Similarity	NPD1607	Approved
0.6226	Remote Similarity	NPD4380	Phase 2
0.6225	Remote Similarity	NPD2438	Suspended
0.6225	Remote Similarity	NPD2531	Phase 2
0.6224	Remote Similarity	NPD8651	Approved
0.6222	Remote Similarity	NPD5535	Approved
0.622	Remote Similarity	NPD5494	Approved
0.6218	Remote Similarity	NPD4661	Approved
0.6218	Remote Similarity	NPD4662	Approved
0.6218	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD1240	Approved
0.6216	Remote Similarity	NPD4060	Phase 1
0.6216	Remote Similarity	NPD3140	Approved
0.6216	Remote Similarity	NPD3142	Approved
0.6214	Remote Similarity	NPD4626	Approved
0.6207	Remote Similarity	NPD2861	Phase 2
0.6207	Remote Similarity	NPD9494	Approved
0.6203	Remote Similarity	NPD7239	Suspended
0.62	Remote Similarity	NPD7097	Phase 1
0.62	Remote Similarity	NPD5688	Approved
0.62	Remote Similarity	NPD5689	Approved
0.6199	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7075	Discontinued
0.619	Remote Similarity	NPD7985	Registered
0.6187	Remote Similarity	NPD9545	Approved
0.6187	Remote Similarity	NPD7741	Discontinued
0.6187	Remote Similarity	NPD3091	Approved
0.6182	Remote Similarity	NPD7199	Phase 2
0.6181	Remote Similarity	NPD1470	Approved
0.6181	Remote Similarity	NPD6362	Approved
0.6174	Remote Similarity	NPD5124	Phase 1
0.6174	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2296	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