NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.24
Volume:	457.767
LogP:	2.537
LogD:	1.672
LogS:	-3.685
# Rotatable Bonds:	9
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	5.004
Fsp3:	0.833
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:	-5.359
MDCK Permeability:	6.0900954849785194e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	69.53600311279297%
Volume Distribution (VD):	0.253
Pgp-substrate:	35.98603439331055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.769
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.468
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	10.355
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.591
Skin Sensitization:	0.08
Carcinogencity:	0.063
Eye Corrosion:	0.012
Eye Irritation:	0.016
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC476717

Natural Product ID:	NPC476717
*Common Name:**	seco-Briarellin R
IUPAC Name:	3-[(4R,5R,9R,12S,13S)-5-butanoyloxy-5,9,12-trimethyl-10-oxo-3-(2-oxopropyl)-2,11-dioxatricyclo[6.4.1.04,13]tridecan-12-yl]propanoic acid
Synonyms:	Seco-Briarellin R
Standard InCHIKey:	BEFLHDZUKXCHNN-UUCBCGJZSA-N
Standard InCHI:	InChI=1S/C24H36O8/c1-6-7-18(28)31-23(4)10-8-15-14(3)22(29)32-24(5,11-9-17(26)27)21-19(15)20(23)16(30-21)12-13(2)25/h14-16,19-21H,6-12H2,1-5H3,(H,26,27)/t14-,15?,16?,19+,20+,21?,23-,24+/m1/s1
SMILES:	CCCC(=O)O[C@@]1(CCC2[C@H](C(=O)O[C@@](C3[C@@H]2[C@@H]1C(O3)CC(=O)C)(C)CCC(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566423
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO33599	Briareum polyanthes	Species	Briareidae	Eukaryota	n.a.	coral reef off Cabo Rojo, Puerto Rico, at a depth of 10-15 m	2000-OCT	PMID[17190449]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	20	ug/ml	PMID[17190449]

☑ 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 NPC476717 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	415
0.1-0.2	3141
0.2-0.3	7907
0.3-0.4	14040
0.4-0.5	7619
0.5-0.6	6826
0.6-0.7	2528
0.7-0.8	204
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC476721
0.8929	High Similarity	NPC476715
0.8588	High Similarity	NPC477434
0.8523	High Similarity	NPC477440
0.8523	High Similarity	NPC477443
0.8427	Intermediate Similarity	NPC477442
0.8427	Intermediate Similarity	NPC477444
0.8427	Intermediate Similarity	NPC477433
0.8409	Intermediate Similarity	NPC471221
0.8333	Intermediate Similarity	NPC216137
0.8193	Intermediate Similarity	NPC476719
0.8182	Intermediate Similarity	NPC228593
0.8182	Intermediate Similarity	NPC477441
0.8182	Intermediate Similarity	NPC235196
0.8161	Intermediate Similarity	NPC65133
0.8111	Intermediate Similarity	NPC67653
0.8111	Intermediate Similarity	NPC471459
0.8095	Intermediate Similarity	NPC191345
0.8095	Intermediate Similarity	NPC252483
0.8072	Intermediate Similarity	NPC474020
0.8068	Intermediate Similarity	NPC477445
0.8023	Intermediate Similarity	NPC211049
0.8023	Intermediate Similarity	NPC119922
0.8023	Intermediate Similarity	NPC116320
0.8	Intermediate Similarity	NPC476435
0.7976	Intermediate Similarity	NPC474003
0.7959	Intermediate Similarity	NPC473701
0.7959	Intermediate Similarity	NPC473526
0.7957	Intermediate Similarity	NPC476722
0.7957	Intermediate Similarity	NPC470424
0.7927	Intermediate Similarity	NPC476718
0.7927	Intermediate Similarity	NPC123122
0.7895	Intermediate Similarity	NPC111348
0.7889	Intermediate Similarity	NPC239938
0.7882	Intermediate Similarity	NPC43463
0.7872	Intermediate Similarity	NPC62407
0.7872	Intermediate Similarity	NPC287354
0.7865	Intermediate Similarity	NPC473350
0.7865	Intermediate Similarity	NPC477205
0.7857	Intermediate Similarity	NPC136424
0.7849	Intermediate Similarity	NPC474379
0.7849	Intermediate Similarity	NPC476189
0.7841	Intermediate Similarity	NPC15091
0.7826	Intermediate Similarity	NPC470114
0.7802	Intermediate Similarity	NPC221993
0.7802	Intermediate Similarity	NPC477614
0.7802	Intermediate Similarity	NPC226491
0.7789	Intermediate Similarity	NPC475765
0.7789	Intermediate Similarity	NPC235109
0.7789	Intermediate Similarity	NPC116683
0.7789	Intermediate Similarity	NPC163685
0.7778	Intermediate Similarity	NPC83242
0.7766	Intermediate Similarity	NPC309127
0.7766	Intermediate Similarity	NPC247877
0.7755	Intermediate Similarity	NPC471254
0.7755	Intermediate Similarity	NPC470172
0.7753	Intermediate Similarity	NPC219535
0.7753	Intermediate Similarity	NPC473299
0.7753	Intermediate Similarity	NPC237938
0.7742	Intermediate Similarity	NPC165180
0.7717	Intermediate Similarity	NPC200580
0.7717	Intermediate Similarity	NPC61688
0.7701	Intermediate Similarity	NPC186594
0.7701	Intermediate Similarity	NPC134227
0.7701	Intermediate Similarity	NPC125366
0.7684	Intermediate Similarity	NPC82633
0.7684	Intermediate Similarity	NPC17336
0.7677	Intermediate Similarity	NPC473406
0.7677	Intermediate Similarity	NPC471253
0.7667	Intermediate Similarity	NPC478111
0.7634	Intermediate Similarity	NPC185529
0.7634	Intermediate Similarity	NPC472146
0.7634	Intermediate Similarity	NPC88337
0.7634	Intermediate Similarity	NPC475211
0.7629	Intermediate Similarity	NPC253995
0.7619	Intermediate Similarity	NPC55508
0.7614	Intermediate Similarity	NPC470154
0.7614	Intermediate Similarity	NPC475743
0.7609	Intermediate Similarity	NPC473319
0.7609	Intermediate Similarity	NPC131104
0.7609	Intermediate Similarity	NPC3032
0.7604	Intermediate Similarity	NPC193785
0.7604	Intermediate Similarity	NPC475785
0.7582	Intermediate Similarity	NPC475729
0.7582	Intermediate Similarity	NPC474215
0.7579	Intermediate Similarity	NPC217567
0.7579	Intermediate Similarity	NPC476716
0.7579	Intermediate Similarity	NPC76136
0.7579	Intermediate Similarity	NPC329713
0.7573	Intermediate Similarity	NPC470622
0.7558	Intermediate Similarity	NPC143250
0.7558	Intermediate Similarity	NPC307865
0.7556	Intermediate Similarity	NPC471044
0.7556	Intermediate Similarity	NPC473336
0.7556	Intermediate Similarity	NPC475689
0.7553	Intermediate Similarity	NPC475878
0.7553	Intermediate Similarity	NPC52756
0.7528	Intermediate Similarity	NPC148740
0.7528	Intermediate Similarity	NPC102156
0.7528	Intermediate Similarity	NPC216800
0.7528	Intermediate Similarity	NPC477447
0.7528	Intermediate Similarity	NPC477446
0.7528	Intermediate Similarity	NPC470155
0.7525	Intermediate Similarity	NPC138908
0.7525	Intermediate Similarity	NPC200957
0.75	Intermediate Similarity	NPC157476
0.75	Intermediate Similarity	NPC472951
0.75	Intermediate Similarity	NPC474755
0.75	Intermediate Similarity	NPC122811
0.75	Intermediate Similarity	NPC472943
0.7475	Intermediate Similarity	NPC298266
0.7475	Intermediate Similarity	NPC259654
0.7475	Intermediate Similarity	NPC178853
0.7475	Intermediate Similarity	NPC98225
0.7451	Intermediate Similarity	NPC166993
0.7449	Intermediate Similarity	NPC472144
0.7426	Intermediate Similarity	NPC88469
0.7419	Intermediate Similarity	NPC191221
0.7419	Intermediate Similarity	NPC201607
0.7419	Intermediate Similarity	NPC476379
0.7419	Intermediate Similarity	NPC56777
0.7416	Intermediate Similarity	NPC470156
0.7412	Intermediate Similarity	NPC215030
0.74	Intermediate Similarity	NPC275990
0.74	Intermediate Similarity	NPC244969
0.74	Intermediate Similarity	NPC80640
0.74	Intermediate Similarity	NPC213528
0.7396	Intermediate Similarity	NPC477495
0.7391	Intermediate Similarity	NPC80700
0.7379	Intermediate Similarity	NPC273155
0.7379	Intermediate Similarity	NPC153587
0.7374	Intermediate Similarity	NPC80417
0.7374	Intermediate Similarity	NPC477656
0.7368	Intermediate Similarity	NPC474065
0.7363	Intermediate Similarity	NPC25037
0.7363	Intermediate Similarity	NPC50438
0.7363	Intermediate Similarity	NPC291310
0.7363	Intermediate Similarity	NPC34984
0.7363	Intermediate Similarity	NPC181871
0.7363	Intermediate Similarity	NPC9060
0.7353	Intermediate Similarity	NPC166079
0.7353	Intermediate Similarity	NPC306776
0.7353	Intermediate Similarity	NPC470587
0.7347	Intermediate Similarity	NPC470632
0.7347	Intermediate Similarity	NPC472145
0.7347	Intermediate Similarity	NPC74466
0.7347	Intermediate Similarity	NPC266417
0.7347	Intermediate Similarity	NPC472273
0.734	Intermediate Similarity	NPC253618
0.734	Intermediate Similarity	NPC24705
0.734	Intermediate Similarity	NPC77001
0.734	Intermediate Similarity	NPC56962
0.7327	Intermediate Similarity	NPC277074
0.7327	Intermediate Similarity	NPC209298
0.732	Intermediate Similarity	NPC322188
0.7317	Intermediate Similarity	NPC469925
0.7312	Intermediate Similarity	NPC263802
0.7312	Intermediate Similarity	NPC314364
0.7312	Intermediate Similarity	NPC470920
0.7308	Intermediate Similarity	NPC16657
0.7308	Intermediate Similarity	NPC274827
0.7308	Intermediate Similarity	NPC204652
0.7308	Intermediate Similarity	NPC87393
0.7303	Intermediate Similarity	NPC60568
0.73	Intermediate Similarity	NPC252614
0.73	Intermediate Similarity	NPC46848
0.73	Intermediate Similarity	NPC236585
0.7294	Intermediate Similarity	NPC109510
0.7283	Intermediate Similarity	NPC131350
0.7283	Intermediate Similarity	NPC474572
0.7283	Intermediate Similarity	NPC93616
0.7282	Intermediate Similarity	NPC112780
0.7273	Intermediate Similarity	NPC274695
0.7273	Intermediate Similarity	NPC474793
0.7273	Intermediate Similarity	NPC475616
0.7273	Intermediate Similarity	NPC470014
0.7273	Intermediate Similarity	NPC211087
0.7273	Intermediate Similarity	NPC471038
0.7273	Intermediate Similarity	NPC17183
0.7273	Intermediate Similarity	NPC475725
0.7264	Intermediate Similarity	NPC157571
0.7263	Intermediate Similarity	NPC18536
0.7263	Intermediate Similarity	NPC50443
0.7263	Intermediate Similarity	NPC470262
0.7255	Intermediate Similarity	NPC100078
0.7255	Intermediate Similarity	NPC301787
0.7255	Intermediate Similarity	NPC470167
0.7255	Intermediate Similarity	NPC65523
0.7255	Intermediate Similarity	NPC267637
0.7253	Intermediate Similarity	NPC30102
0.7253	Intermediate Similarity	NPC128816
0.7253	Intermediate Similarity	NPC227170
0.7253	Intermediate Similarity	NPC67158
0.7245	Intermediate Similarity	NPC256227
0.7245	Intermediate Similarity	NPC476728
0.7245	Intermediate Similarity	NPC477264
0.7238	Intermediate Similarity	NPC66513
0.7238	Intermediate Similarity	NPC137104
0.7238	Intermediate Similarity	NPC475463
0.7238	Intermediate Similarity	NPC474786

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 NPC476717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	510
0.1-0.2	3565
0.2-0.3	3255
0.3-0.4	1057
0.4-0.5	428
0.5-0.6	275
0.6-0.7	59
0.7-0.8	1
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
0.7475	Intermediate Similarity	NPD1700	Approved
0.7253	Intermediate Similarity	NPD3669	Approved
0.7253	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1780	Approved
0.7222	Intermediate Similarity	NPD1779	Approved
0.7212	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6697	Approved
0.6889	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD6115	Approved
0.6889	Remote Similarity	NPD6114	Approved
0.6778	Remote Similarity	NPD6116	Phase 1
0.6762	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3703	Phase 2
0.6703	Remote Similarity	NPD4238	Approved
0.6703	Remote Similarity	NPD4802	Phase 2
0.6667	Remote Similarity	NPD6117	Approved
0.6609	Remote Similarity	NPD6921	Approved
0.6549	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7492	Approved
0.6437	Remote Similarity	NPD229	Approved
0.6415	Remote Similarity	NPD8086	Approved
0.6415	Remote Similarity	NPD8082	Approved
0.6415	Remote Similarity	NPD8138	Approved
0.6415	Remote Similarity	NPD8083	Approved
0.6415	Remote Similarity	NPD8085	Approved
0.6415	Remote Similarity	NPD8139	Approved
0.6415	Remote Similarity	NPD8084	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6374	Remote Similarity	NPD3702	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD8328	Phase 3
0.6355	Remote Similarity	NPD8276	Approved
0.6355	Remote Similarity	NPD8275	Approved
0.6353	Remote Similarity	NPD7909	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6337	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.6296	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8081	Approved
0.6296	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7736	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6264	Remote Similarity	NPD1810	Approved
0.6264	Remote Similarity	NPD1811	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD6008	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD8393	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6222	Remote Similarity	NPD5777	Approved
0.6222	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8513	Phase 3
0.6186	Remote Similarity	NPD8515	Approved
0.6186	Remote Similarity	NPD8516	Approved
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD8517	Approved
0.6186	Remote Similarity	NPD6016	Approved
0.6182	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7983	Approved
0.6163	Remote Similarity	NPD371	Approved
0.614	Remote Similarity	NPD8133	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6134	Remote Similarity	NPD5988	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6126	Remote Similarity	NPD6881	Approved
0.6126	Remote Similarity	NPD6899	Approved
0.6117	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD5778	Approved
0.6117	Remote Similarity	NPD6399	Phase 3
0.6111	Remote Similarity	NPD2686	Approved
0.6111	Remote Similarity	NPD2687	Approved
0.6111	Remote Similarity	NPD2254	Approved
0.6098	Remote Similarity	NPD7319	Approved
0.6067	Remote Similarity	NPD5360	Phase 3
0.6067	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6882	Approved
0.6049	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6081	Approved
0.6038	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD5701	Approved
0.6036	Remote Similarity	NPD5697	Approved
0.6023	Remote Similarity	NPD4224	Phase 2
0.6018	Remote Similarity	NPD7102	Approved
0.6018	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD7507	Approved
0.5983	Remote Similarity	NPD6009	Approved
0.5983	Remote Similarity	NPD7115	Discovery
0.5981	Remote Similarity	NPD4225	Approved
0.598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6101	Approved
0.5965	Remote Similarity	NPD6617	Approved
0.5965	Remote Similarity	NPD6847	Approved
0.5965	Remote Similarity	NPD6869	Approved
0.5965	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD7604	Phase 2
0.5935	Remote Similarity	NPD8074	Phase 3
0.5934	Remote Similarity	NPD4244	Approved
0.5934	Remote Similarity	NPD4245	Approved
0.5929	Remote Similarity	NPD6013	Approved
0.5929	Remote Similarity	NPD6012	Approved
0.5929	Remote Similarity	NPD6014	Approved
0.5918	Remote Similarity	NPD6435	Approved
0.5918	Remote Similarity	NPD7345	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5913	Remote Similarity	NPD6053	Discontinued
0.5909	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5282	Discontinued
0.5905	Remote Similarity	NPD7748	Approved
0.59	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD8140	Approved
0.5893	Remote Similarity	NPD8307	Discontinued
0.5887	Remote Similarity	NPD6033	Approved
0.5882	Remote Similarity	NPD3198	Approved
0.5882	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4634	Approved
0.5877	Remote Similarity	NPD6371	Approved
0.5865	Remote Similarity	NPD6411	Approved
0.5854	Remote Similarity	NPD3728	Approved
0.5854	Remote Similarity	NPD3730	Approved
0.5854	Remote Similarity	NPD6336	Discontinued
0.5849	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6686	Approved
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD7638	Approved
0.5826	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3698	Phase 2
0.5824	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD8301	Approved
0.5818	Remote Similarity	NPD8300	Approved
0.5816	Remote Similarity	NPD5369	Approved
0.581	Remote Similarity	NPD8171	Discontinued
0.5789	Remote Similarity	NPD8306	Approved
0.5789	Remote Similarity	NPD8305	Approved
0.578	Remote Similarity	NPD7640	Approved
0.578	Remote Similarity	NPD7639	Approved
0.5778	Remote Similarity	NPD896	Approved
0.5778	Remote Similarity	NPD898	Approved
0.5778	Remote Similarity	NPD897	Approved
0.5769	Remote Similarity	NPD46	Approved
0.5769	Remote Similarity	NPD6698	Approved
0.5763	Remote Similarity	NPD6940	Discontinued
0.5761	Remote Similarity	NPD4789	Approved
0.5755	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7900	Approved
0.5752	Remote Similarity	NPD6412	Phase 2
0.5741	Remote Similarity	NPD4755	Approved
0.5739	Remote Similarity	NPD8087	Discontinued
0.5714	Remote Similarity	NPD5368	Approved
0.5714	Remote Similarity	NPD73	Approved
0.5714	Remote Similarity	NPD6928	Phase 2
0.5714	Remote Similarity	NPD7515	Phase 2
0.5699	Remote Similarity	NPD4758	Discontinued
0.5686	Remote Similarity	NPD5786	Approved
0.5676	Remote Similarity	NPD7632	Discontinued
0.5673	Remote Similarity	NPD5328	Approved
0.567	Remote Similarity	NPD3671	Phase 1
0.567	Remote Similarity	NPD5364	Discontinued
0.5663	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD8267	Approved
0.5656	Remote Similarity	NPD8269	Approved
0.5656	Remote Similarity	NPD8268	Approved
0.5656	Remote Similarity	NPD8266	Approved
0.5647	Remote Similarity	NPD8959	Approved
0.5636	Remote Similarity	NPD4700	Approved
0.5636	Remote Similarity	NPD4696	Approved
0.5636	Remote Similarity	NPD5285	Approved
0.5636	Remote Similarity	NPD8418	Phase 2
0.5636	Remote Similarity	NPD5286	Approved
0.563	Remote Similarity	NPD6274	Approved
0.562	Remote Similarity	NPD7101	Approved
0.562	Remote Similarity	NPD7100	Approved
0.5612	Remote Similarity	NPD7329	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