NPASS Compound

Structure

NPC474166 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.2699 2.8520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4994 0.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8320 5.8058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1870 4.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1061 -1.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0036 1.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7744 -1.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 3.3392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3432 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 3.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3432 2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3432 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3432 2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4994 1.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2593 5.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3432 4.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1371 -1.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0829 3.3392 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4994 3.0381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7705 0.7883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6556 1.5765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0829 0.7883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7705 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6556 2.5509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7098 5.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3432 5.4740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4357 -2.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0716 -1.7149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6556 4.1275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4994 4.0124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6556 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3432 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 25 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 14 21 1 0 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 32 1 0 0 0 0 17 29 2 0 0 0 0 17 33 1 0 0 0 0 18 24 1 1 0 0 0 18 31 1 0 0 0 0 19 24 1 1 0 0 0 19 32 1 0 0 0 0 20 26 1 1 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 6 0 0 0 22 26 1 1 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 6 1 6 0 0 0 25 26 1 1 0 0 0 25 35 1 0 0 0 0 26 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.22
Volume:	487.32
LogP:	3.067
LogD:	2.506
LogS:	-4.357
# Rotatable Bonds:	6
TPSA:	117.73
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.886
Fsp3:	0.692
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:	-5.138
MDCK Permeability:	0.00010800952441059053
Pgp-inhibitor:	0.999
Pgp-substrate:	0.555
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.852
Plasma Protein Binding (PPB):	64.62000274658203%
Volume Distribution (VD):	1.727
Pgp-substrate:	36.88666534423828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.717
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	3.899
Half-life (T1/2):	0.608

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.56
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.501
Carcinogencity:	0.523
Eye Corrosion:	0.11
Eye Irritation:	0.078
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC474166

Natural Product ID:	NPC474166
*Common Name:**	Briareolide H
IUPAC Name:	n.a.
Synonyms:	Briareolide H
Standard InCHIKey:	GBZASDFVUGDNRC-ISFMLNJISA-N
Standard InCHI:	InChI=1S/C26H34O9/c1-13-8-10-18(31-15(3)27)24(6)19(32-16(4)28)11-9-14(2)21(24)22(33-17(5)29)26-20(12-13)34-23(30)25(26,7)35-26/h9,12,18-22H,8,10-11H2,1-7H3/b13-12-/t18-,19+,20+,21-,22-,24+,25-,26+/m1/s1
SMILES:	CC1=CC2C3(C(C4C(=CCC(C4(C(CC1)OC(=O)C)C)OC(=O)C)C)OC(=O)C)C(O3)(C(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463137
PubChem CID:	44584199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.1	ug ml-1	PMID[527138]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[527138]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[527138]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.29	ug ml-1	PMID[527138]

☑ 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 NPC474166 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	258
0.1-0.2	1576
0.2-0.3	5421
0.3-0.4	12558
0.4-0.5	10901
0.5-0.6	7327
0.6-0.7	3861
0.7-0.8	666
0.8-0.85	71
0.85-0.9	35
0.9-0.95	21
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19239
0.95	High Similarity	NPC475922
0.9495	High Similarity	NPC475510
0.9495	High Similarity	NPC475587
0.9406	High Similarity	NPC115257
0.9406	High Similarity	NPC161816
0.94	High Similarity	NPC473595
0.94	High Similarity	NPC473939
0.9216	High Similarity	NPC474586
0.9216	High Similarity	NPC281624
0.9216	High Similarity	NPC473843
0.9216	High Similarity	NPC473975
0.9216	High Similarity	NPC473594
0.92	High Similarity	NPC16313
0.92	High Similarity	NPC475802
0.92	High Similarity	NPC9303
0.9126	High Similarity	NPC194619
0.9109	High Similarity	NPC326994
0.9109	High Similarity	NPC324327
0.9109	High Similarity	NPC72813
0.9109	High Similarity	NPC194620
0.9109	High Similarity	NPC474421
0.9091	High Similarity	NPC183571
0.9038	High Similarity	NPC473877
0.902	High Similarity	NPC14862
0.902	High Similarity	NPC169888
0.902	High Similarity	NPC474664
0.902	High Similarity	NPC233379
0.902	High Similarity	NPC55972
0.902	High Similarity	NPC327286
0.9	High Similarity	NPC69171
0.9	High Similarity	NPC474165
0.8932	High Similarity	NPC15218
0.8835	High Similarity	NPC94377
0.8812	High Similarity	NPC4620
0.8785	High Similarity	NPC474333
0.875	High Similarity	NPC42662
0.8725	High Similarity	NPC220964
0.8725	High Similarity	NPC475676
0.8704	High Similarity	NPC296822
0.8687	High Similarity	NPC471140
0.844	Intermediate Similarity	NPC476710
0.844	Intermediate Similarity	NPC476711
0.8431	Intermediate Similarity	NPC264477
0.8431	Intermediate Similarity	NPC477511
0.84	Intermediate Similarity	NPC17585
0.8364	Intermediate Similarity	NPC476712
0.8364	Intermediate Similarity	NPC476713
0.8351	Intermediate Similarity	NPC475971
0.8349	Intermediate Similarity	NPC73314
0.8333	Intermediate Similarity	NPC317687
0.8283	Intermediate Similarity	NPC476597
0.8283	Intermediate Similarity	NPC476598
0.8273	Intermediate Similarity	NPC477509
0.8252	Intermediate Similarity	NPC164598
0.8252	Intermediate Similarity	NPC474339
0.8252	Intermediate Similarity	NPC476478
0.8241	Intermediate Similarity	NPC317107
0.82	Intermediate Similarity	NPC476596
0.819	Intermediate Similarity	NPC471143
0.819	Intermediate Similarity	NPC477510
0.8173	Intermediate Similarity	NPC471148
0.8155	Intermediate Similarity	NPC477512
0.8144	Intermediate Similarity	NPC266957
0.8131	Intermediate Similarity	NPC322903
0.8108	Intermediate Similarity	NPC270478
0.8091	Intermediate Similarity	NPC477126
0.8081	Intermediate Similarity	NPC475748
0.8058	Intermediate Similarity	NPC264378
0.8053	Intermediate Similarity	NPC470186
0.8041	Intermediate Similarity	NPC50637
0.8037	Intermediate Similarity	NPC477513
0.802	Intermediate Similarity	NPC471147
0.8019	Intermediate Similarity	NPC477127
0.8	Intermediate Similarity	NPC105725
0.8	Intermediate Similarity	NPC20713
0.8	Intermediate Similarity	NPC471933
0.7981	Intermediate Similarity	NPC475949
0.798	Intermediate Similarity	NPC151770
0.7959	Intermediate Similarity	NPC476600
0.7944	Intermediate Similarity	NPC470979
0.7944	Intermediate Similarity	NPC470975
0.7944	Intermediate Similarity	NPC103088
0.7941	Intermediate Similarity	NPC475659
0.7928	Intermediate Similarity	NPC159333
0.7909	Intermediate Similarity	NPC475495
0.789	Intermediate Similarity	NPC471934
0.789	Intermediate Similarity	NPC469370
0.7885	Intermediate Similarity	NPC208233
0.7885	Intermediate Similarity	NPC222303
0.7876	Intermediate Similarity	NPC473590
0.787	Intermediate Similarity	NPC474716
0.7864	Intermediate Similarity	NPC279621
0.7864	Intermediate Similarity	NPC230800
0.7864	Intermediate Similarity	NPC473859
0.785	Intermediate Similarity	NPC146731
0.785	Intermediate Similarity	NPC258532
0.785	Intermediate Similarity	NPC472756
0.7845	Intermediate Similarity	NPC310035
0.7845	Intermediate Similarity	NPC188222
0.7845	Intermediate Similarity	NPC282003
0.7843	Intermediate Similarity	NPC473330
0.7843	Intermediate Similarity	NPC476267
0.7843	Intermediate Similarity	NPC140543
0.7843	Intermediate Similarity	NPC473316
0.7838	Intermediate Similarity	NPC473522
0.7838	Intermediate Similarity	NPC475277
0.7838	Intermediate Similarity	NPC477093
0.783	Intermediate Similarity	NPC472754
0.783	Intermediate Similarity	NPC149371
0.783	Intermediate Similarity	NPC49393
0.7818	Intermediate Similarity	NPC253906
0.781	Intermediate Similarity	NPC288876
0.78	Intermediate Similarity	NPC166919
0.7798	Intermediate Similarity	NPC476479
0.7789	Intermediate Similarity	NPC474739
0.7778	Intermediate Similarity	NPC123726
0.7778	Intermediate Similarity	NPC67251
0.7778	Intermediate Similarity	NPC284365
0.7778	Intermediate Similarity	NPC231889
0.7778	Intermediate Similarity	NPC303006
0.7757	Intermediate Similarity	NPC475321
0.7757	Intermediate Similarity	NPC472755
0.7745	Intermediate Similarity	NPC165383
0.7739	Intermediate Similarity	NPC475520
0.7736	Intermediate Similarity	NPC201718
0.7736	Intermediate Similarity	NPC47880
0.7736	Intermediate Similarity	NPC472753
0.7736	Intermediate Similarity	NPC471767
0.7736	Intermediate Similarity	NPC98225
0.7719	Intermediate Similarity	NPC469684
0.7714	Intermediate Similarity	NPC470188
0.7714	Intermediate Similarity	NPC471144
0.7706	Intermediate Similarity	NPC180744
0.7692	Intermediate Similarity	NPC35498
0.7692	Intermediate Similarity	NPC476315
0.7685	Intermediate Similarity	NPC474741
0.7685	Intermediate Similarity	NPC296950
0.7679	Intermediate Similarity	NPC269530
0.7672	Intermediate Similarity	NPC475003
0.767	Intermediate Similarity	NPC148463
0.767	Intermediate Similarity	NPC161998
0.767	Intermediate Similarity	NPC474247
0.7664	Intermediate Similarity	NPC471757
0.7664	Intermediate Similarity	NPC250594
0.7664	Intermediate Similarity	NPC78127
0.7664	Intermediate Similarity	NPC474709
0.7658	Intermediate Similarity	NPC472215
0.7658	Intermediate Similarity	NPC472214
0.7658	Intermediate Similarity	NPC475134
0.7658	Intermediate Similarity	NPC5103
0.7658	Intermediate Similarity	NPC475563
0.7652	Intermediate Similarity	NPC470776
0.7652	Intermediate Similarity	NPC473720
0.7647	Intermediate Similarity	NPC233437
0.7647	Intermediate Similarity	NPC49420
0.7647	Intermediate Similarity	NPC207641
0.7636	Intermediate Similarity	NPC151393
0.7632	Intermediate Similarity	NPC474734
0.7627	Intermediate Similarity	NPC91693
0.7627	Intermediate Similarity	NPC265557
0.7627	Intermediate Similarity	NPC18945
0.7627	Intermediate Similarity	NPC105926
0.7624	Intermediate Similarity	NPC471222
0.7623	Intermediate Similarity	NPC470185
0.7611	Intermediate Similarity	NPC469463
0.7611	Intermediate Similarity	NPC469496
0.7611	Intermediate Similarity	NPC469454
0.7611	Intermediate Similarity	NPC473535
0.7611	Intermediate Similarity	NPC33360
0.7596	Intermediate Similarity	NPC471141
0.7589	Intermediate Similarity	NPC304180
0.7589	Intermediate Similarity	NPC179798
0.7589	Intermediate Similarity	NPC473921
0.7589	Intermediate Similarity	NPC475668
0.7589	Intermediate Similarity	NPC475480
0.7576	Intermediate Similarity	NPC38468
0.7576	Intermediate Similarity	NPC50362
0.7576	Intermediate Similarity	NPC319795
0.7573	Intermediate Similarity	NPC475657
0.7573	Intermediate Similarity	NPC228451
0.7573	Intermediate Similarity	NPC476300
0.7573	Intermediate Similarity	NPC475838
0.7573	Intermediate Similarity	NPC125674
0.757	Intermediate Similarity	NPC207885
0.7568	Intermediate Similarity	NPC475191
0.7568	Intermediate Similarity	NPC87335
0.7568	Intermediate Similarity	NPC474242
0.7565	Intermediate Similarity	NPC470775
0.7565	Intermediate Similarity	NPC176513
0.7565	Intermediate Similarity	NPC475305
0.7565	Intermediate Similarity	NPC471146
0.7565	Intermediate Similarity	NPC53396
0.7565	Intermediate Similarity	NPC98249
0.7563	Intermediate Similarity	NPC470922
0.7563	Intermediate Similarity	NPC24651
0.7563	Intermediate Similarity	NPC476729
0.7551	Intermediate Similarity	NPC12283
0.7551	Intermediate Similarity	NPC474703
0.7551	Intermediate Similarity	NPC475989

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 NPC474166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2146
0.2-0.3	3817
0.3-0.4	2012
0.4-0.5	593
0.5-0.6	274
0.6-0.7	76
0.7-0.8	5
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
0.7576	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD46	Approved
0.7379	Intermediate Similarity	NPD6698	Approved
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6371	Approved
0.7119	Intermediate Similarity	NPD7115	Discovery
0.7115	Intermediate Similarity	NPD1695	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7018	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD5282	Discontinued
0.6991	Remote Similarity	NPD6008	Approved
0.6983	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7983	Approved
0.6803	Remote Similarity	NPD6319	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5778	Approved
0.6759	Remote Similarity	NPD5779	Approved
0.6759	Remote Similarity	NPD6399	Phase 3
0.6748	Remote Similarity	NPD8513	Phase 3
0.6748	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD8517	Approved
0.6748	Remote Similarity	NPD8515	Approved
0.6729	Remote Similarity	NPD7838	Discovery
0.672	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD6672	Approved
0.6698	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.664	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD8297	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7078	Approved
0.6614	Remote Similarity	NPD8293	Discontinued
0.6607	Remote Similarity	NPD7638	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6566	Remote Similarity	NPD8039	Approved
0.6562	Remote Similarity	NPD7736	Approved
0.656	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD6649	Approved
0.6555	Remote Similarity	NPD6650	Approved
0.6552	Remote Similarity	NPD6675	Approved
0.6552	Remote Similarity	NPD5739	Approved
0.6552	Remote Similarity	NPD6402	Approved
0.6552	Remote Similarity	NPD7128	Approved
0.6549	Remote Similarity	NPD7639	Approved
0.6549	Remote Similarity	NPD7640	Approved
0.6518	Remote Similarity	NPD6083	Phase 2
0.6518	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD6411	Approved
0.6512	Remote Similarity	NPD7319	Approved
0.6509	Remote Similarity	NPD6098	Approved
0.65	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD5695	Phase 3
0.6484	Remote Similarity	NPD8074	Phase 3
0.6481	Remote Similarity	NPD6904	Approved
0.6481	Remote Similarity	NPD6673	Approved
0.6481	Remote Similarity	NPD6080	Approved
0.648	Remote Similarity	NPD6015	Approved
0.648	Remote Similarity	NPD6016	Approved
0.646	Remote Similarity	NPD5696	Approved
0.6441	Remote Similarity	NPD7320	Approved
0.6441	Remote Similarity	NPD6881	Approved
0.6441	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD5988	Approved
0.6422	Remote Similarity	NPD5785	Approved
0.6412	Remote Similarity	NPD7260	Phase 2
0.6406	Remote Similarity	NPD7507	Approved
0.6396	Remote Similarity	NPD7900	Approved
0.6396	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6356	Remote Similarity	NPD5697	Approved
0.6356	Remote Similarity	NPD5701	Approved
0.6355	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD6409	Approved
0.6355	Remote Similarity	NPD5330	Approved
0.6355	Remote Similarity	NPD6684	Approved
0.6355	Remote Similarity	NPD7146	Approved
0.6355	Remote Similarity	NPD7521	Approved
0.6349	Remote Similarity	NPD6921	Approved
0.6339	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7290	Approved
0.6333	Remote Similarity	NPD6883	Approved
0.6333	Remote Similarity	NPD7102	Approved
0.633	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6051	Approved
0.6316	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4632	Approved
0.6311	Remote Similarity	NPD8133	Approved
0.629	Remote Similarity	NPD6009	Approved
0.6286	Remote Similarity	NPD5209	Approved
0.6281	Remote Similarity	NPD6847	Approved
0.6281	Remote Similarity	NPD6869	Approved
0.6281	Remote Similarity	NPD6617	Approved
0.6281	Remote Similarity	NPD8130	Phase 1
0.6273	Remote Similarity	NPD5692	Phase 3
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6013	Approved
0.6241	Remote Similarity	NPD6845	Suspended
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7902	Approved
0.622	Remote Similarity	NPD5983	Phase 2
0.6218	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5694	Approved
0.6207	Remote Similarity	NPD1700	Approved
0.619	Remote Similarity	NPD5369	Approved
0.6183	Remote Similarity	NPD6033	Approved
0.6176	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD8273	Phase 1
0.6154	Remote Similarity	NPD6336	Discontinued
0.6148	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4251	Approved
0.6147	Remote Similarity	NPD4250	Approved
0.614	Remote Similarity	NPD7839	Suspended
0.6132	Remote Similarity	NPD4270	Approved
0.6132	Remote Similarity	NPD4269	Approved
0.6111	Remote Similarity	NPD7327	Approved
0.6111	Remote Similarity	NPD7328	Approved
0.6106	Remote Similarity	NPD7748	Approved
0.6094	Remote Similarity	NPD8033	Approved
0.6075	Remote Similarity	NPD7154	Phase 3
0.6066	Remote Similarity	NPD4634	Approved
0.6063	Remote Similarity	NPD7516	Approved
0.6055	Remote Similarity	NPD5786	Approved
0.6055	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD3668	Phase 3
0.6017	Remote Similarity	NPD7632	Discontinued
0.6016	Remote Similarity	NPD8294	Approved
0.6016	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5982	Remote Similarity	NPD5207	Approved
0.5981	Remote Similarity	NPD3667	Approved
0.5979	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5956	Approved
0.5969	Remote Similarity	NPD8296	Approved
0.5969	Remote Similarity	NPD8335	Approved
0.5969	Remote Similarity	NPD8380	Approved
0.5969	Remote Similarity	NPD7503	Approved
0.5969	Remote Similarity	NPD8379	Approved
0.5969	Remote Similarity	NPD8378	Approved
0.5965	Remote Similarity	NPD6001	Approved
0.5963	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5363	Approved
0.5952	Remote Similarity	NPD6274	Approved
0.5948	Remote Similarity	NPD5959	Approved
0.5948	Remote Similarity	NPD4755	Approved
0.5943	Remote Similarity	NPD4822	Approved
0.5943	Remote Similarity	NPD4821	Approved
0.5943	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4820	Approved
0.5943	Remote Similarity	NPD4252	Approved
0.5943	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD7100	Approved
0.5938	Remote Similarity	NPD7101	Approved
0.5929	Remote Similarity	NPD8035	Phase 2
0.5929	Remote Similarity	NPD8034	Phase 2
0.5929	Remote Similarity	NPD7515	Phase 2
0.5926	Remote Similarity	NPD5362	Discontinued
0.5926	Remote Similarity	NPD6110	Phase 1
0.5913	Remote Similarity	NPD5654	Approved
0.5909	Remote Similarity	NPD8451	Approved
0.5905	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4753	Phase 2
0.5887	Remote Similarity	NPD2204	Approved
0.5882	Remote Similarity	NPD5211	Phase 2
0.5878	Remote Similarity	NPD7830	Approved
0.5878	Remote Similarity	NPD7829	Approved
0.5872	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8448	Approved
0.5859	Remote Similarity	NPD6335	Approved
0.5856	Remote Similarity	NPD7524	Approved
0.5856	Remote Similarity	NPD3573	Approved
0.5847	Remote Similarity	NPD5286	Approved
0.5847	Remote Similarity	NPD4700	Approved
0.5847	Remote Similarity	NPD5285	Approved
0.5847	Remote Similarity	NPD4696	Approved
0.5846	Remote Similarity	NPD6909	Approved
0.5846	Remote Similarity	NPD6908	Approved
0.5841	Remote Similarity	NPD3168	Discontinued
0.5833	Remote Similarity	NPD6435	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