NPASS Compound

Structure

NPC168883 OpenBabel07101719252D 36 38 0 0 1 0 0 0 0 0999 V2000 -4.2191 -5.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3566 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1748 -1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3310 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 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 -1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 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 -3.3753 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6620 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 -2.3054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 15 1 0 0 0 0 4 25 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 18 23 1 0 0 0 0 19 18 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 31 1 0 0 0 0 22 28 1 0 0 0 0 22 32 2 0 0 0 0 23 25 1 0 0 0 0 23 33 2 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 34 2 0 0 0 0 25 28 1 1 0 0 0 26 5 1 1 0 0 0 26 35 1 0 0 0 0 27 6 1 6 0 0 0 27 36 1 0 0 0 0 28 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.23
Volume:	513.768
LogP:	1.987
LogD:	1.5
LogS:	-4.174
# Rotatable Bonds:	7
TPSA:	142.88
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	6.304
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.667
MDCK Permeability:	7.976976485224441e-05
Pgp-inhibitor:	0.449
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	92.35533905029297%
Volume Distribution (VD):	0.894
Pgp-substrate:	8.44859790802002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.659
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	6.233
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.593
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.785
Skin Sensitization:	0.207
Carcinogencity:	0.935
Eye Corrosion:	0.95
Eye Irritation:	0.345
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC168883

Natural Product ID:	NPC168883
*Common Name:**	Bisvertinoquinol
IUPAC Name:	(1R,2S,6S,7S,8S,10S,11Z)-2-[(E)-hex-4-enoyl]-5,6,10-trihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-1,4,6,10-tetramethyl-7,8-dihydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-diene-3,9,12-trione
Synonyms:	Bisvertinoquinol
Standard InCHIKey:	ZXWVVZIMJSPORF-QOXNXBNCSA-N
Standard InCHI:	InChI=1S/C28H34O8/c1-7-9-11-13-16(29)18-19-20-27(6,36)21(31)15(3)22(32)28(20,17(30)14-12-10-8-2)25(4,23(18)33)24(34)26(19,5)35/h7-11,13,19-20,29,31,35-36H,12,14H2,1-6H3/b9-7+,10-8+,13-11+,18-16-/t19-,20-,25-,26+,27+,28-/m1/s1
SMILES:	C/C=C/CCC(=O)[C@]12C(=O)C(=C([C@@]([C@H]1[C@H]1/C(=C(C=CC=CC)/O)/C(=O)[C@]2(C)C(=O)[C@@]1(C)O)(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464564
PubChem CID:	44584002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32492	penicillium notatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[509003]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[509003]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[509003]

☑ 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 NPC168883 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	262
0.1-0.2	1406
0.2-0.3	4266
0.3-0.4	8374
0.4-0.5	14765
0.5-0.6	8462
0.6-0.7	4602
0.7-0.8	552
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC300026
0.8318	Intermediate Similarity	NPC85529
0.8318	Intermediate Similarity	NPC32006
0.82	Intermediate Similarity	NPC474918
0.8125	Intermediate Similarity	NPC108721
0.8125	Intermediate Similarity	NPC73300
0.8091	Intermediate Similarity	NPC11710
0.8073	Intermediate Similarity	NPC475060
0.8073	Intermediate Similarity	NPC220229
0.8058	Intermediate Similarity	NPC196227
0.802	Intermediate Similarity	NPC472688
0.802	Intermediate Similarity	NPC472676
0.8	Intermediate Similarity	NPC217201
0.7982	Intermediate Similarity	NPC85829
0.7982	Intermediate Similarity	NPC49958
0.7982	Intermediate Similarity	NPC50692
0.7982	Intermediate Similarity	NPC97202
0.7982	Intermediate Similarity	NPC48733
0.7982	Intermediate Similarity	NPC214264
0.7982	Intermediate Similarity	NPC260268
0.7982	Intermediate Similarity	NPC149047
0.7982	Intermediate Similarity	NPC319077
0.7982	Intermediate Similarity	NPC302607
0.7982	Intermediate Similarity	NPC166607
0.7982	Intermediate Similarity	NPC202167
0.7982	Intermediate Similarity	NPC296945
0.7982	Intermediate Similarity	NPC171137
0.7982	Intermediate Similarity	NPC150531
0.7982	Intermediate Similarity	NPC152695
0.7982	Intermediate Similarity	NPC476027
0.7965	Intermediate Similarity	NPC474271
0.7928	Intermediate Similarity	NPC214644
0.7909	Intermediate Similarity	NPC83744
0.7909	Intermediate Similarity	NPC165873
0.789	Intermediate Similarity	NPC160843
0.789	Intermediate Similarity	NPC209502
0.789	Intermediate Similarity	NPC204833
0.7885	Intermediate Similarity	NPC472976
0.7885	Intermediate Similarity	NPC472977
0.7876	Intermediate Similarity	NPC193948
0.7864	Intermediate Similarity	NPC116726
0.7863	Intermediate Similarity	NPC109973
0.785	Intermediate Similarity	NPC46761
0.7838	Intermediate Similarity	NPC329417
0.7822	Intermediate Similarity	NPC471792
0.781	Intermediate Similarity	NPC272617
0.7807	Intermediate Similarity	NPC471204
0.7798	Intermediate Similarity	NPC249187
0.7798	Intermediate Similarity	NPC230918
0.7798	Intermediate Similarity	NPC247957
0.7788	Intermediate Similarity	NPC188738
0.7768	Intermediate Similarity	NPC87335
0.7768	Intermediate Similarity	NPC141350
0.7748	Intermediate Similarity	NPC185
0.7748	Intermediate Similarity	NPC477916
0.7736	Intermediate Similarity	NPC269492
0.7714	Intermediate Similarity	NPC258674
0.7712	Intermediate Similarity	NPC478051
0.7706	Intermediate Similarity	NPC477915
0.7699	Intermediate Similarity	NPC210005
0.7699	Intermediate Similarity	NPC286880
0.7692	Intermediate Similarity	NPC251310
0.7679	Intermediate Similarity	NPC154608
0.7679	Intermediate Similarity	NPC295244
0.7679	Intermediate Similarity	NPC192813
0.7679	Intermediate Similarity	NPC277017
0.7672	Intermediate Similarity	NPC478216
0.767	Intermediate Similarity	NPC65615
0.767	Intermediate Similarity	NPC68148
0.7664	Intermediate Similarity	NPC474938
0.7664	Intermediate Similarity	NPC472690
0.7664	Intermediate Similarity	NPC474785
0.7664	Intermediate Similarity	NPC477268
0.7664	Intermediate Similarity	NPC273269
0.7664	Intermediate Similarity	NPC477267
0.7664	Intermediate Similarity	NPC472689
0.7658	Intermediate Similarity	NPC257353
0.7658	Intermediate Similarity	NPC51452
0.7658	Intermediate Similarity	NPC323834
0.7656	Intermediate Similarity	NPC471672
0.7652	Intermediate Similarity	NPC962
0.7652	Intermediate Similarity	NPC250109
0.7642	Intermediate Similarity	NPC53565
0.7642	Intermediate Similarity	NPC476245
0.7636	Intermediate Similarity	NPC191892
0.7636	Intermediate Similarity	NPC320294
0.7632	Intermediate Similarity	NPC472928
0.7615	Intermediate Similarity	NPC470184
0.7607	Intermediate Similarity	NPC471854
0.7603	Intermediate Similarity	NPC476729
0.7593	Intermediate Similarity	NPC103051
0.7589	Intermediate Similarity	NPC230541
0.7589	Intermediate Similarity	NPC3316
0.7589	Intermediate Similarity	NPC144854
0.7586	Intermediate Similarity	NPC247069
0.7583	Intermediate Similarity	NPC222688
0.7573	Intermediate Similarity	NPC48107
0.757	Intermediate Similarity	NPC473164
0.7568	Intermediate Similarity	NPC72255
0.7568	Intermediate Similarity	NPC65523
0.7565	Intermediate Similarity	NPC207251
0.7565	Intermediate Similarity	NPC90769
0.7565	Intermediate Similarity	NPC472002
0.7547	Intermediate Similarity	NPC470957
0.7547	Intermediate Similarity	NPC473162
0.7547	Intermediate Similarity	NPC470958
0.7547	Intermediate Similarity	NPC160413
0.7544	Intermediate Similarity	NPC76084
0.7542	Intermediate Similarity	NPC318751
0.7542	Intermediate Similarity	NPC21326
0.7525	Intermediate Similarity	NPC251170
0.7524	Intermediate Similarity	NPC472978
0.7523	Intermediate Similarity	NPC154072
0.7522	Intermediate Similarity	NPC293850
0.7522	Intermediate Similarity	NPC65941
0.7521	Intermediate Similarity	NPC18945
0.7521	Intermediate Similarity	NPC96312
0.7521	Intermediate Similarity	NPC105926
0.7521	Intermediate Similarity	NPC266728
0.7521	Intermediate Similarity	NPC265557
0.7521	Intermediate Similarity	NPC67251
0.7521	Intermediate Similarity	NPC474734
0.7521	Intermediate Similarity	NPC49492
0.7521	Intermediate Similarity	NPC328374
0.7521	Intermediate Similarity	NPC251236
0.7521	Intermediate Similarity	NPC179626
0.7521	Intermediate Similarity	NPC91693
0.7521	Intermediate Similarity	NPC40632
0.75	Intermediate Similarity	NPC161147
0.75	Intermediate Similarity	NPC469463
0.75	Intermediate Similarity	NPC472973
0.75	Intermediate Similarity	NPC292588
0.75	Intermediate Similarity	NPC118011
0.75	Intermediate Similarity	NPC36668
0.75	Intermediate Similarity	NPC473161
0.75	Intermediate Similarity	NPC49451
0.75	Intermediate Similarity	NPC102352
0.75	Intermediate Similarity	NPC181357
0.75	Intermediate Similarity	NPC469454
0.75	Intermediate Similarity	NPC317210
0.75	Intermediate Similarity	NPC478052
0.75	Intermediate Similarity	NPC469496
0.75	Intermediate Similarity	NPC198539
0.7479	Intermediate Similarity	NPC268958
0.7478	Intermediate Similarity	NPC179798
0.7478	Intermediate Similarity	NPC304180
0.7478	Intermediate Similarity	NPC34315
0.7477	Intermediate Similarity	NPC275583
0.7477	Intermediate Similarity	NPC131366
0.7477	Intermediate Similarity	NPC147232
0.7477	Intermediate Similarity	NPC473170
0.7477	Intermediate Similarity	NPC271195
0.7477	Intermediate Similarity	NPC251017
0.7477	Intermediate Similarity	NPC311612
0.7476	Intermediate Similarity	NPC476409
0.7459	Intermediate Similarity	NPC24651
0.7456	Intermediate Similarity	NPC220705
0.7453	Intermediate Similarity	NPC131840
0.7438	Intermediate Similarity	NPC312833
0.7436	Intermediate Similarity	NPC326542
0.7436	Intermediate Similarity	NPC473798
0.7429	Intermediate Similarity	NPC134321
0.7429	Intermediate Similarity	NPC473099
0.7414	Intermediate Similarity	NPC264634
0.7414	Intermediate Similarity	NPC474516
0.7414	Intermediate Similarity	NPC147180
0.7411	Intermediate Similarity	NPC284865
0.7411	Intermediate Similarity	NPC325769
0.7411	Intermediate Similarity	NPC40170
0.7407	Intermediate Similarity	NPC61369
0.7407	Intermediate Similarity	NPC471463
0.7407	Intermediate Similarity	NPC5532
0.7407	Intermediate Similarity	NPC249954
0.7407	Intermediate Similarity	NPC469545
0.7404	Intermediate Similarity	NPC158778
0.7404	Intermediate Similarity	NPC58271
0.74	Intermediate Similarity	NPC225515
0.74	Intermediate Similarity	NPC226068
0.7398	Intermediate Similarity	NPC225049
0.7395	Intermediate Similarity	NPC470776
0.7395	Intermediate Similarity	NPC311554
0.7395	Intermediate Similarity	NPC257457
0.7395	Intermediate Similarity	NPC17772
0.7391	Intermediate Similarity	NPC473036
0.7391	Intermediate Similarity	NPC272898
0.7387	Intermediate Similarity	NPC87351
0.7387	Intermediate Similarity	NPC473424
0.7387	Intermediate Similarity	NPC234892
0.7383	Intermediate Similarity	NPC103527
0.7383	Intermediate Similarity	NPC196485
0.7383	Intermediate Similarity	NPC245972
0.7383	Intermediate Similarity	NPC473172
0.7383	Intermediate Similarity	NPC478089
0.7383	Intermediate Similarity	NPC474328
0.7383	Intermediate Similarity	NPC474690
0.7383	Intermediate Similarity	NPC474882
0.7383	Intermediate Similarity	NPC299100
0.7379	Intermediate Similarity	NPC472985
0.7379	Intermediate Similarity	NPC239685
0.7379	Intermediate Similarity	NPC472986

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 NPC168883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	1540
0.2-0.3	3682
0.3-0.4	2442
0.4-0.5	789
0.5-0.6	264
0.6-0.7	170
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
0.7387	Intermediate Similarity	NPD5211	Phase 2
0.73	Intermediate Similarity	NPD4695	Discontinued
0.7257	Intermediate Similarity	NPD5141	Approved
0.7248	Intermediate Similarity	NPD4697	Phase 3
0.7241	Intermediate Similarity	NPD4634	Approved
0.7207	Intermediate Similarity	NPD4696	Approved
0.7207	Intermediate Similarity	NPD5285	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.7182	Intermediate Similarity	NPD4755	Approved
0.7179	Intermediate Similarity	NPD6650	Approved
0.7179	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4633	Approved
0.708	Intermediate Similarity	NPD5225	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD4700	Approved
0.7048	Intermediate Similarity	NPD4519	Discontinued
0.7048	Intermediate Similarity	NPD4623	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD5173	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7018	Intermediate Similarity	NPD5175	Approved
0.7009	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD5210	Approved
0.6975	Remote Similarity	NPD8297	Approved
0.6952	Remote Similarity	NPD5329	Approved
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6897	Remote Similarity	NPD6402	Approved
0.6897	Remote Similarity	NPD5739	Approved
0.6897	Remote Similarity	NPD6675	Approved
0.6897	Remote Similarity	NPD7128	Approved
0.6897	Remote Similarity	NPD4768	Approved
0.6897	Remote Similarity	NPD4767	Approved
0.6887	Remote Similarity	NPD4694	Approved
0.6887	Remote Similarity	NPD5280	Approved
0.6887	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5281	Approved
0.6881	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD4754	Approved
0.6857	Remote Similarity	NPD4197	Approved
0.6855	Remote Similarity	NPD6319	Approved
0.6846	Remote Similarity	NPD7260	Phase 2
0.6838	Remote Similarity	NPD5697	Approved
0.6833	Remote Similarity	NPD6882	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.6807	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD5248	Approved
0.6807	Remote Similarity	NPD7102	Approved
0.6807	Remote Similarity	NPD6883	Approved
0.6807	Remote Similarity	NPD7290	Approved
0.6807	Remote Similarity	NPD5249	Phase 3
0.6807	Remote Similarity	NPD5250	Approved
0.6807	Remote Similarity	NPD5251	Approved
0.678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6011	Approved
0.678	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD3617	Approved
0.675	Remote Similarity	NPD6847	Approved
0.675	Remote Similarity	NPD6869	Approved
0.675	Remote Similarity	NPD6617	Approved
0.675	Remote Similarity	NPD8130	Phase 1
0.6748	Remote Similarity	NPD7115	Discovery
0.6748	Remote Similarity	NPD6009	Approved
0.6729	Remote Similarity	NPD5690	Phase 2
0.6727	Remote Similarity	NPD7515	Phase 2
0.6723	Remote Similarity	NPD6014	Approved
0.6723	Remote Similarity	NPD6013	Approved
0.6723	Remote Similarity	NPD6012	Approved
0.672	Remote Similarity	NPD6054	Approved
0.6697	Remote Similarity	NPD4753	Phase 2
0.6695	Remote Similarity	NPD5701	Approved
0.6693	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5128	Approved
0.6638	Remote Similarity	NPD5091	Approved
0.6636	Remote Similarity	NPD1696	Phase 3
0.6614	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD5217	Approved
0.6612	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5216	Approved
0.6612	Remote Similarity	NPD5127	Approved
0.6612	Remote Similarity	NPD5215	Approved
0.661	Remote Similarity	NPD6008	Approved
0.6607	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7748	Approved
0.6607	Remote Similarity	NPD7900	Approved
0.6587	Remote Similarity	NPD6059	Approved
0.6574	Remote Similarity	NPD5279	Phase 3
0.6562	Remote Similarity	NPD7604	Phase 2
0.6542	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD5983	Phase 2
0.6535	Remote Similarity	NPD6016	Approved
0.6518	Remote Similarity	NPD5779	Approved
0.6518	Remote Similarity	NPD5778	Approved
0.6512	Remote Similarity	NPD7492	Approved
0.6509	Remote Similarity	NPD3667	Approved
0.65	Remote Similarity	NPD5168	Approved
0.6484	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7639	Approved
0.6466	Remote Similarity	NPD7640	Approved
0.6462	Remote Similarity	NPD6336	Discontinued
0.6462	Remote Similarity	NPD6616	Approved
0.6452	Remote Similarity	NPD5167	Approved
0.6446	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD5694	Approved
0.6429	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD6050	Approved
0.6422	Remote Similarity	NPD4689	Approved
0.6422	Remote Similarity	NPD5205	Approved
0.6422	Remote Similarity	NPD4690	Approved
0.6422	Remote Similarity	NPD4688	Approved
0.6422	Remote Similarity	NPD4138	Approved
0.6422	Remote Similarity	NPD4693	Phase 3
0.6418	Remote Similarity	NPD6845	Suspended
0.6417	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7078	Approved
0.6396	Remote Similarity	NPD6904	Approved
0.6396	Remote Similarity	NPD6673	Approved
0.6396	Remote Similarity	NPD6080	Approved
0.6389	Remote Similarity	NPD3666	Approved
0.6389	Remote Similarity	NPD3665	Phase 1
0.6389	Remote Similarity	NPD3133	Approved
0.6379	Remote Similarity	NPD7638	Approved
0.6378	Remote Similarity	NPD7100	Approved
0.6378	Remote Similarity	NPD7101	Approved
0.6372	Remote Similarity	NPD5133	Approved
0.6364	Remote Similarity	NPD7736	Approved
0.6349	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6317	Approved
0.6348	Remote Similarity	NPD7614	Phase 1
0.6339	Remote Similarity	NPD5692	Phase 3
0.6336	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD5282	Discontinued
0.6306	Remote Similarity	NPD6672	Approved
0.6306	Remote Similarity	NPD5737	Approved
0.6306	Remote Similarity	NPD4518	Approved
0.6299	Remote Similarity	NPD6314	Approved
0.6299	Remote Similarity	NPD6313	Approved
0.6296	Remote Similarity	NPD6110	Phase 1
0.6288	Remote Similarity	NPD8293	Discontinued
0.6283	Remote Similarity	NPD6411	Approved
0.6283	Remote Similarity	NPD5693	Phase 1
0.6281	Remote Similarity	NPD6412	Phase 2
0.6279	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6921	Approved
0.6279	Remote Similarity	NPD8517	Approved
0.6279	Remote Similarity	NPD8513	Phase 3
0.6279	Remote Similarity	NPD8515	Approved
0.6279	Remote Similarity	NPD8516	Approved
0.627	Remote Similarity	NPD6868	Approved
0.627	Remote Similarity	NPD6274	Approved
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5695	Phase 3
0.6241	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD3668	Phase 3
0.6239	Remote Similarity	NPD4225	Approved
0.623	Remote Similarity	NPD6686	Approved
0.6226	Remote Similarity	NPD4195	Approved
0.6214	Remote Similarity	NPD4058	Approved
0.6195	Remote Similarity	NPD5207	Approved
0.6195	Remote Similarity	NPD4096	Approved
0.6194	Remote Similarity	NPD7319	Approved
0.6162	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD6908	Approved
0.6154	Remote Similarity	NPD6909	Approved
0.6154	Remote Similarity	NPD7503	Approved
0.6148	Remote Similarity	NPD6614	Approved
0.614	Remote Similarity	NPD7983	Approved
0.6126	Remote Similarity	NPD6098	Approved
0.6124	Remote Similarity	NPD4522	Approved
0.6106	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6101	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