NPASS Compound

Structure

CID130275 OpenBabel06191715492D 23 26 0 0 1 0 0 0 0 0999 V2000 3.3867 -0.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -2.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5178 -3.3899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 -2.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5170 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1961 -3.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0337 -1.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3568 -2.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3566 -1.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 -1.9374 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8387 -0.4842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8387 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 -1.4527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8390 -1.4532 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7375 1.4474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7234 0.0903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0340 -2.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	3.747
LogD:	3.591
LogS:	-4.08
# Rotatable Bonds:	1
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	4.289
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.339
MDCK Permeability:	2.1748224753537215e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	95.25202178955078%
Volume Distribution (VD):	1.301
Pgp-substrate:	4.012118816375732%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.616
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.414
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.467
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	2.816
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.276
Skin Sensitization:	0.25
Carcinogencity:	0.428
Eye Corrosion:	0.339
Eye Irritation:	0.772
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC130275

Natural Product ID:	NPC130275
*Common Name:**	Spongia-13(16),14-Dien-19-Oic Acid
IUPAC Name:	(3bR,5aR,6S,9aR,9bR)-3b,6,9a-trimethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[2,1-e][2]benzofuran-6-carboxylic acid
Synonyms:
Standard InCHIKey:	KJCLDWYEUKTPNA-ZRSLWSEBSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-18-10-7-16-19(2,8-4-9-20(16,3)17(21)22)15(18)6-5-13-11-23-12-14(13)18/h11-12,15-16H,4-10H2,1-3H3,(H,21,22)/t15-,16+,18-,19+,20-/m0/s1
SMILES:	OC(=O)[C@@]1(C)CCC[C@]2([C@H]1CC[C@@]1([C@@H]2CCc2c1coc2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510050
PubChem CID:	21582644
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
NPO29103	Spongia matamata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075761]
NPO30943	Spongia	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057748]
NPO30943	Spongia	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22129061]
NPO40357	Spongia ceylonensis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27526327]
NPO40357	Spongia ceylonensis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28026175]
NPO29103	Spongia matamata	Species	Spongiidae	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	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	uM	PMID[544893]
NPT140	Organism	Artemia	Artemia	LC50	=	10.0	ug.mL-1	PMID[544892]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[544894]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	100.0	%	PMID[544894]

☑ 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 NPC130275 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	225
0.1-0.2	1241
0.2-0.3	2690
0.3-0.4	6193
0.4-0.5	12473
0.5-0.6	13752
0.6-0.7	5341
0.7-0.8	639
0.8-0.85	97
0.85-0.9	28
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC36255
0.9587	High Similarity	NPC120836
0.9587	High Similarity	NPC223063
0.9576	High Similarity	NPC272899
0.9496	High Similarity	NPC83115
0.9417	High Similarity	NPC230979
0.9417	High Similarity	NPC303010
0.9397	High Similarity	NPC212918
0.9339	High Similarity	NPC46536
0.9339	High Similarity	NPC138139
0.9187	High Similarity	NPC207294
0.9187	High Similarity	NPC112706
0.9113	High Similarity	NPC198904
0.9106	High Similarity	NPC83178
0.9091	High Similarity	NPC16922
0.9024	High Similarity	NPC74612
0.8968	High Similarity	NPC89133
0.8943	High Similarity	NPC179354
0.8906	High Similarity	NPC471998
0.8871	High Similarity	NPC23086
0.8855	High Similarity	NPC202260
0.875	High Similarity	NPC471995
0.874	High Similarity	NPC476925
0.873	High Similarity	NPC327527
0.873	High Similarity	NPC476917
0.8626	High Similarity	NPC214572
0.8583	High Similarity	NPC477040
0.8583	High Similarity	NPC329707
0.8561	High Similarity	NPC4764
0.8561	High Similarity	NPC307401
0.8561	High Similarity	NPC310043
0.856	High Similarity	NPC243269
0.8548	High Similarity	NPC477967
0.8527	High Similarity	NPC61788
0.8468	Intermediate Similarity	NPC97566
0.8467	Intermediate Similarity	NPC41182
0.8443	Intermediate Similarity	NPC144745
0.8443	Intermediate Similarity	NPC208906
0.8438	Intermediate Similarity	NPC477123
0.8438	Intermediate Similarity	NPC477966
0.8433	Intermediate Similarity	NPC90953
0.843	Intermediate Similarity	NPC150895
0.8413	Intermediate Similarity	NPC178382
0.8409	Intermediate Similarity	NPC476947
0.8397	Intermediate Similarity	NPC218838
0.8394	Intermediate Similarity	NPC476944
0.8385	Intermediate Similarity	NPC298190
0.8382	Intermediate Similarity	NPC121158
0.8358	Intermediate Similarity	NPC471996
0.8358	Intermediate Similarity	NPC476943
0.8346	Intermediate Similarity	NPC46896
0.8345	Intermediate Similarity	NPC216755
0.8321	Intermediate Similarity	NPC267632
0.8295	Intermediate Similarity	NPC477039
0.8284	Intermediate Similarity	NPC42400
0.8284	Intermediate Similarity	NPC310830
0.8271	Intermediate Similarity	NPC158525
0.8261	Intermediate Similarity	NPC251865
0.8258	Intermediate Similarity	NPC293253
0.8248	Intermediate Similarity	NPC62103
0.8248	Intermediate Similarity	NPC263337
0.8248	Intermediate Similarity	NPC20578
0.8235	Intermediate Similarity	NPC148374
0.8235	Intermediate Similarity	NPC56197
0.8226	Intermediate Similarity	NPC243704
0.8217	Intermediate Similarity	NPC246392
0.8217	Intermediate Similarity	NPC290955
0.8214	Intermediate Similarity	NPC471174
0.8209	Intermediate Similarity	NPC146872
0.8169	Intermediate Similarity	NPC228842
0.8169	Intermediate Similarity	NPC212257
0.8154	Intermediate Similarity	NPC26532
0.8143	Intermediate Similarity	NPC346
0.8134	Intermediate Similarity	NPC92941
0.8125	Intermediate Similarity	NPC477965
0.8125	Intermediate Similarity	NPC477038
0.812	Intermediate Similarity	NPC470740
0.812	Intermediate Similarity	NPC471006
0.811	Intermediate Similarity	NPC317217
0.8102	Intermediate Similarity	NPC67003
0.8099	Intermediate Similarity	NPC234494
0.8092	Intermediate Similarity	NPC208389
0.8088	Intermediate Similarity	NPC220094
0.8085	Intermediate Similarity	NPC255414
0.8085	Intermediate Similarity	NPC250228
0.8058	Intermediate Similarity	NPC103134
0.8056	Intermediate Similarity	NPC121615
0.8056	Intermediate Similarity	NPC294511
0.8056	Intermediate Similarity	NPC472672
0.8045	Intermediate Similarity	NPC471817
0.8043	Intermediate Similarity	NPC205765
0.8042	Intermediate Similarity	NPC470997
0.8028	Intermediate Similarity	NPC476941
0.8028	Intermediate Similarity	NPC476942
0.8028	Intermediate Similarity	NPC93666
0.8015	Intermediate Similarity	NPC470742
0.8015	Intermediate Similarity	NPC279877
0.8	Intermediate Similarity	NPC253201
0.8	Intermediate Similarity	NPC142113
0.8	Intermediate Similarity	NPC237259
0.8	Intermediate Similarity	NPC34421
0.8	Intermediate Similarity	NPC238843
0.8	Intermediate Similarity	NPC302054
0.8	Intermediate Similarity	NPC199044
0.8	Intermediate Similarity	NPC98206
0.7986	Intermediate Similarity	NPC272590
0.7986	Intermediate Similarity	NPC52412
0.7972	Intermediate Similarity	NPC195325
0.7972	Intermediate Similarity	NPC211625
0.7972	Intermediate Similarity	NPC69647
0.7972	Intermediate Similarity	NPC472654
0.7972	Intermediate Similarity	NPC125182
0.7958	Intermediate Similarity	NPC476938
0.7958	Intermediate Similarity	NPC476937
0.7958	Intermediate Similarity	NPC71821
0.7956	Intermediate Similarity	NPC236532
0.7955	Intermediate Similarity	NPC59502
0.7943	Intermediate Similarity	NPC290038
0.7943	Intermediate Similarity	NPC185456
0.7939	Intermediate Similarity	NPC476016
0.7931	Intermediate Similarity	NPC246164
0.7931	Intermediate Similarity	NPC33938
0.7931	Intermediate Similarity	NPC469503
0.7929	Intermediate Similarity	NPC243577
0.7929	Intermediate Similarity	NPC476946
0.7923	Intermediate Similarity	NPC474829
0.7923	Intermediate Similarity	NPC300098
0.7923	Intermediate Similarity	NPC290193
0.792	Intermediate Similarity	NPC79202
0.792	Intermediate Similarity	NPC59035
0.791	Intermediate Similarity	NPC473982
0.7902	Intermediate Similarity	NPC471007
0.7891	Intermediate Similarity	NPC41880
0.7891	Intermediate Similarity	NPC104736
0.7887	Intermediate Similarity	NPC471292
0.7887	Intermediate Similarity	NPC262198
0.7887	Intermediate Similarity	NPC233763
0.7886	Intermediate Similarity	NPC1811
0.7886	Intermediate Similarity	NPC26157
0.7883	Intermediate Similarity	NPC170604
0.7883	Intermediate Similarity	NPC215109
0.7879	Intermediate Similarity	NPC474279
0.7879	Intermediate Similarity	NPC474438
0.7877	Intermediate Similarity	NPC30222
0.7877	Intermediate Similarity	NPC44606
0.7877	Intermediate Similarity	NPC282445
0.7877	Intermediate Similarity	NPC178932
0.7863	Intermediate Similarity	NPC474260
0.7863	Intermediate Similarity	NPC81912
0.7863	Intermediate Similarity	NPC329694
0.7863	Intermediate Similarity	NPC329922
0.7857	Intermediate Similarity	NPC227660
0.7846	Intermediate Similarity	NPC188377
0.7846	Intermediate Similarity	NPC65735
0.7846	Intermediate Similarity	NPC118853
0.7842	Intermediate Similarity	NPC90296
0.7838	Intermediate Similarity	NPC195954
0.7838	Intermediate Similarity	NPC304692
0.7838	Intermediate Similarity	NPC194499
0.7838	Intermediate Similarity	NPC88007
0.7838	Intermediate Similarity	NPC7059
0.7832	Intermediate Similarity	NPC302987
0.7823	Intermediate Similarity	NPC281258
0.7823	Intermediate Similarity	NPC296807
0.7823	Intermediate Similarity	NPC155939
0.7823	Intermediate Similarity	NPC35000
0.7823	Intermediate Similarity	NPC141538
0.7823	Intermediate Similarity	NPC92979
0.7823	Intermediate Similarity	NPC469336
0.7817	Intermediate Similarity	NPC56731
0.7817	Intermediate Similarity	NPC5676
0.7808	Intermediate Similarity	NPC268905
0.7808	Intermediate Similarity	NPC475777
0.7808	Intermediate Similarity	NPC75906
0.7805	Intermediate Similarity	NPC105249
0.7803	Intermediate Similarity	NPC319140
0.7803	Intermediate Similarity	NPC95567
0.7803	Intermediate Similarity	NPC474830
0.7801	Intermediate Similarity	NPC64568
0.7801	Intermediate Similarity	NPC205071
0.7795	Intermediate Similarity	NPC87466
0.7786	Intermediate Similarity	NPC20500
0.7786	Intermediate Similarity	NPC71274
0.7786	Intermediate Similarity	NPC471559
0.7786	Intermediate Similarity	NPC471074
0.7786	Intermediate Similarity	NPC473885
0.7786	Intermediate Similarity	NPC75557
0.7785	Intermediate Similarity	NPC474611
0.7762	Intermediate Similarity	NPC62799
0.7755	Intermediate Similarity	NPC114880
0.7755	Intermediate Similarity	NPC57998
0.7734	Intermediate Similarity	NPC473969
0.7733	Intermediate Similarity	NPC335761
0.7733	Intermediate Similarity	NPC287559
0.7733	Intermediate Similarity	NPC8389
0.7724	Intermediate Similarity	NPC95526
0.7724	Intermediate Similarity	NPC471001
0.7724	Intermediate Similarity	NPC470998
0.7721	Intermediate Similarity	NPC474425
0.7721	Intermediate Similarity	NPC474426

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 NPC130275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	938
0.2-0.3	1792
0.3-0.4	2758
0.4-0.5	2145
0.5-0.6	1089
0.6-0.7	217
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
0.7899	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6273	Approved
0.7584	Intermediate Similarity	NPD5761	Phase 2
0.7584	Intermediate Similarity	NPD5760	Phase 2
0.7361	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD8032	Phase 2
0.7246	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7214	Intermediate Similarity	NPD4140	Approved
0.7206	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2313	Discontinued
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD6765	Approved
0.6994	Remote Similarity	NPD6764	Approved
0.6985	Remote Similarity	NPD1608	Approved
0.6974	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3268	Approved
0.6947	Remote Similarity	NPD5951	Approved
0.6943	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5585	Approved
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6906	Remote Similarity	NPD2798	Approved
0.6897	Remote Similarity	NPD4308	Phase 3
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8434	Phase 2
0.6879	Remote Similarity	NPD7008	Discontinued
0.6866	Remote Similarity	NPD1894	Discontinued
0.6861	Remote Similarity	NPD3972	Approved
0.6849	Remote Similarity	NPD4476	Approved
0.6849	Remote Similarity	NPD4477	Approved
0.6831	Remote Similarity	NPD6798	Discontinued
0.6831	Remote Similarity	NPD3764	Approved
0.6826	Remote Similarity	NPD6784	Approved
0.6826	Remote Similarity	NPD6785	Approved
0.6809	Remote Similarity	NPD6832	Phase 2
0.6803	Remote Similarity	NPD2344	Approved
0.6788	Remote Similarity	NPD1281	Approved
0.6783	Remote Similarity	NPD6663	Approved
0.6769	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD17	Approved
0.6765	Remote Similarity	NPD1778	Approved
0.6763	Remote Similarity	NPD1876	Approved
0.6761	Remote Similarity	NPD7095	Approved
0.6753	Remote Similarity	NPD3226	Approved
0.675	Remote Similarity	NPD8127	Discontinued
0.6738	Remote Similarity	NPD5736	Approved
0.6736	Remote Similarity	NPD2979	Phase 3
0.6736	Remote Similarity	NPD4307	Phase 2
0.6735	Remote Similarity	NPD1551	Phase 2
0.6714	Remote Similarity	NPD3266	Approved
0.6714	Remote Similarity	NPD3267	Approved
0.6713	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2533	Approved
0.6711	Remote Similarity	NPD2534	Approved
0.6711	Remote Similarity	NPD2532	Approved
0.6691	Remote Similarity	NPD4359	Approved
0.6691	Remote Similarity	NPD5327	Phase 3
0.6689	Remote Similarity	NPD6002	Phase 3
0.6689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6005	Phase 3
0.6689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1471	Phase 3
0.6689	Remote Similarity	NPD6004	Phase 3
0.6688	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.6644	Remote Similarity	NPD4534	Discontinued
0.6642	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7427	Discontinued
0.6623	Remote Similarity	NPD2309	Approved
0.6622	Remote Similarity	NPD6100	Approved
0.6622	Remote Similarity	NPD6099	Approved
0.6622	Remote Similarity	NPD2935	Discontinued
0.6619	Remote Similarity	NPD9717	Approved
0.6617	Remote Similarity	NPD1241	Discontinued
0.6604	Remote Similarity	NPD7768	Phase 2
0.6603	Remote Similarity	NPD6599	Discontinued
0.6596	Remote Similarity	NPD1203	Approved
0.6579	Remote Similarity	NPD7440	Discontinued
0.6579	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7236	Approved
0.6577	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4622	Approved
0.6575	Remote Similarity	NPD4618	Approved
0.6575	Remote Similarity	NPD5735	Approved
0.6573	Remote Similarity	NPD2614	Approved
0.6569	Remote Similarity	NPD5691	Approved
0.6562	Remote Similarity	NPD3749	Approved
0.6561	Remote Similarity	NPD7411	Suspended
0.6554	Remote Similarity	NPD3748	Approved
0.6541	Remote Similarity	NPD5535	Approved
0.6536	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5958	Discontinued
0.6531	Remote Similarity	NPD6353	Approved
0.6522	Remote Similarity	NPD4626	Approved
0.6522	Remote Similarity	NPD3019	Approved
0.6516	Remote Similarity	NPD920	Approved
0.651	Remote Similarity	NPD2531	Phase 2
0.651	Remote Similarity	NPD2438	Suspended
0.6507	Remote Similarity	NPD4060	Phase 1
0.6497	Remote Similarity	NPD7028	Phase 2
0.6494	Remote Similarity	NPD642	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1243	Approved
0.649	Remote Similarity	NPD2800	Approved
0.6489	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2182	Approved
0.6488	Remote Similarity	NPD6559	Discontinued
0.6486	Remote Similarity	NPD5689	Approved
0.6486	Remote Similarity	NPD5688	Approved
0.6486	Remote Similarity	NPD7097	Phase 1
0.6483	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3496	Discontinued
0.6467	Remote Similarity	NPD5763	Approved
0.6467	Remote Similarity	NPD5762	Approved
0.6463	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6677	Suspended
0.6449	Remote Similarity	NPD1651	Approved
0.6446	Remote Similarity	NPD7177	Discontinued
0.6444	Remote Similarity	NPD2629	Approved
0.6443	Remote Similarity	NPD7033	Discontinued
0.6438	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4870	Approved
0.6438	Remote Similarity	NPD4062	Phase 3
0.6434	Remote Similarity	NPD4624	Approved
0.6434	Remote Similarity	NPD5647	Approved
0.6434	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5909	Discontinued
0.6424	Remote Similarity	NPD2897	Discontinued
0.6424	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD37	Approved
0.641	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5844	Phase 1
0.6403	Remote Similarity	NPD2932	Approved
0.64	Remote Similarity	NPD2796	Approved
0.6398	Remote Similarity	NPD4965	Approved
0.6398	Remote Similarity	NPD4966	Approved
0.6398	Remote Similarity	NPD4967	Phase 2
0.6397	Remote Similarity	NPD4198	Discontinued
0.6387	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1481	Phase 2
0.6378	Remote Similarity	NPD1238	Approved
0.6377	Remote Similarity	NPD9545	Approved
0.637	Remote Similarity	NPD7985	Registered
0.637	Remote Similarity	NPD411	Approved
0.6369	Remote Similarity	NPD7239	Suspended
0.6364	Remote Similarity	NPD6362	Approved
0.6358	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7075	Discontinued
0.6357	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3847	Discontinued
0.6351	Remote Similarity	NPD1933	Approved
0.6346	Remote Similarity	NPD5049	Phase 3
0.6336	Remote Similarity	NPD3134	Approved
0.6325	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6799	Approved
0.6319	Remote Similarity	NPD6234	Discontinued
0.6319	Remote Similarity	NPD1019	Discontinued
0.6316	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7577	Discontinued
0.6312	Remote Similarity	NPD6287	Discontinued
0.6312	Remote Similarity	NPD1535	Discovery
0.6309	Remote Similarity	NPD6653	Approved
0.6306	Remote Similarity	NPD3873	Phase 3
0.6306	Remote Similarity	NPD3869	Phase 3
0.6304	Remote Similarity	NPD7644	Approved
0.6303	Remote Similarity	NPD7229	Phase 3
0.6299	Remote Similarity	NPD2354	Approved
0.6299	Remote Similarity	NPD3887	Approved
0.6296	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7094	Approved
0.6296	Remote Similarity	NPD6858	Approved
0.6294	Remote Similarity	NPD3225	Approved
0.6284	Remote Similarity	NPD3620	Phase 2
0.6284	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7157	Approved
0.6264	Remote Similarity	NPD7693	Approved
0.6259	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD447	Suspended
0.6242	Remote Similarity	NPD6959	Discontinued
0.6242	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7199	Phase 2
0.6242	Remote Similarity	NPD5124	Phase 1

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