NPASS Compound

Structure

NPC475461 OpenBabel07101718292D 26 27 0 0 1 0 0 0 0 0999 V2000 -2.6396 5.6352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2238 3.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3321 3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8116 -1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8364 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6886 5.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9309 2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8765 1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4807 4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9254 2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 -0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6685 2.1180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4697 0.2263 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0649 2.3917 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5296 4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5346 2.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2135 4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 3.0608 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	0.729
LogD:	1.108
LogS:	-2.717
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.142
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971
MDCK Permeability:	1.8212169379694387e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.558
Plasma Protein Binding (PPB):	69.63284301757812%
Volume Distribution (VD):	0.602
Pgp-substrate:	23.09699821472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	6.531
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.667
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.147
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC475461

Natural Product ID:	NPC475461
*Common Name:**	Hydroxyisonobilin
IUPAC Name:	[(10E)-7,9-dihydroxy-10-methyl-3,6-dimethylidene-2-oxo-4,5,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
Synonyms:	Hydroxyisonobilin
Standard InCHIKey:	SDFKKMBWIQKUOQ-ANGAUAEMSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-6-10(2)19(23)25-16-7-11(3)14(21)9-15(22)12(4)8-17-18(16)13(5)20(24)26-17/h6,8,14-18,21-22H,3,5,7,9H2,1-2,4H3/b10-6+,12-8+
SMILES:	CC=C(C)C(=O)OC1CC(=C)C(CC(C(=CC2C1C(=C)C(=O)O2)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506067
PubChem CID:	6438562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.7	umol/L	PMID[555548]

☑ 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 NPC475461 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	173
0.1-0.2	1073
0.2-0.3	4528
0.3-0.4	10489
0.4-0.5	13487
0.5-0.6	7004
0.6-0.7	4297
0.7-0.8	1357
0.8-0.85	147
0.85-0.9	74
0.9-0.95	48
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC305475
0.9875	High Similarity	NPC255307
0.975	High Similarity	NPC191476
0.975	High Similarity	NPC114979
0.9625	High Similarity	NPC131669
0.9625	High Similarity	NPC169575
0.9625	High Similarity	NPC40746
0.9625	High Similarity	NPC473390
0.9512	High Similarity	NPC150755
0.9506	High Similarity	NPC476804
0.9506	High Similarity	NPC141193
0.9506	High Similarity	NPC96259
0.95	High Similarity	NPC229825
0.939	High Similarity	NPC470755
0.9375	High Similarity	NPC24417
0.9302	High Similarity	NPC125674
0.9302	High Similarity	NPC228451
0.9302	High Similarity	NPC475838
0.9294	High Similarity	NPC469368
0.9294	High Similarity	NPC475855
0.9286	High Similarity	NPC476805
0.9268	High Similarity	NPC158756
0.9195	High Similarity	NPC474247
0.9157	High Similarity	NPC165162
0.9146	High Similarity	NPC59097
0.9136	High Similarity	NPC52861
0.9125	High Similarity	NPC98557
0.9125	High Similarity	NPC167881
0.907	High Similarity	NPC144133
0.907	High Similarity	NPC179394
0.9059	High Similarity	NPC475819
0.9059	High Similarity	NPC476803
0.9048	High Similarity	NPC469910
0.9	High Similarity	NPC93763
0.9	High Similarity	NPC471465
0.9	High Similarity	NPC196653
0.9	High Similarity	NPC108816
0.8989	High Similarity	NPC279621
0.8989	High Similarity	NPC230800
0.8916	High Similarity	NPC116543
0.8889	High Similarity	NPC270126
0.8889	High Similarity	NPC89128
0.8875	High Similarity	NPC171204
0.8875	High Similarity	NPC141789
0.8875	High Similarity	NPC116177
0.8875	High Similarity	NPC320630
0.8875	High Similarity	NPC476028
0.8875	High Similarity	NPC7563
0.8864	High Similarity	NPC295204
0.8864	High Similarity	NPC475302
0.8864	High Similarity	NPC162205
0.8864	High Similarity	NPC288240
0.8864	High Similarity	NPC273579
0.8851	High Similarity	NPC129419
0.8795	High Similarity	NPC89555
0.878	High Similarity	NPC281132
0.875	High Similarity	NPC473321
0.875	High Similarity	NPC235906
0.875	High Similarity	NPC68819
0.8736	High Similarity	NPC218927
0.8736	High Similarity	NPC474032
0.8736	High Similarity	NPC206001
0.8736	High Similarity	NPC295312
0.8736	High Similarity	NPC268298
0.8706	High Similarity	NPC261380
0.8696	High Similarity	NPC288876
0.8675	High Similarity	NPC141810
0.8675	High Similarity	NPC301477
0.8675	High Similarity	NPC25684
0.8675	High Similarity	NPC281949
0.8667	High Similarity	NPC304886
0.8667	High Similarity	NPC471141
0.8667	High Similarity	NPC471142
0.8659	High Similarity	NPC470244
0.8659	High Similarity	NPC470239
0.8652	High Similarity	NPC475912
0.8652	High Similarity	NPC469645
0.8652	High Similarity	NPC469692
0.8636	High Similarity	NPC473619
0.8636	High Similarity	NPC474232
0.8621	High Similarity	NPC473715
0.8621	High Similarity	NPC477302
0.8621	High Similarity	NPC136879
0.8605	High Similarity	NPC50637
0.8556	High Similarity	NPC303942
0.8556	High Similarity	NPC57405
0.8556	High Similarity	NPC121825
0.8556	High Similarity	NPC474338
0.8537	High Similarity	NPC267231
0.8523	High Similarity	NPC166919
0.8506	High Similarity	NPC160138
0.85	High Similarity	NPC476355
0.8471	Intermediate Similarity	NPC250315
0.8471	Intermediate Similarity	NPC474703
0.8462	Intermediate Similarity	NPC477922
0.8462	Intermediate Similarity	NPC14961
0.8462	Intermediate Similarity	NPC270013
0.8462	Intermediate Similarity	NPC36954
0.8452	Intermediate Similarity	NPC470241
0.8452	Intermediate Similarity	NPC325031
0.8434	Intermediate Similarity	NPC617
0.8427	Intermediate Similarity	NPC473448
0.8415	Intermediate Similarity	NPC97516
0.8415	Intermediate Similarity	NPC476794
0.8415	Intermediate Similarity	NPC470240
0.8409	Intermediate Similarity	NPC202672
0.8395	Intermediate Similarity	NPC155587
0.8391	Intermediate Similarity	NPC469483
0.8391	Intermediate Similarity	NPC107787
0.8391	Intermediate Similarity	NPC261721
0.8387	Intermediate Similarity	NPC473326
0.8387	Intermediate Similarity	NPC187268
0.8387	Intermediate Similarity	NPC141191
0.8375	Intermediate Similarity	NPC58956
0.8375	Intermediate Similarity	NPC295633
0.8375	Intermediate Similarity	NPC269206
0.8372	Intermediate Similarity	NPC115786
0.8372	Intermediate Similarity	NPC82297
0.837	Intermediate Similarity	NPC477921
0.837	Intermediate Similarity	NPC476315
0.837	Intermediate Similarity	NPC473859
0.8353	Intermediate Similarity	NPC85772
0.8352	Intermediate Similarity	NPC474035
0.8352	Intermediate Similarity	NPC81386
0.8352	Intermediate Similarity	NPC477131
0.8333	Intermediate Similarity	NPC111114
0.8333	Intermediate Similarity	NPC300312
0.8333	Intermediate Similarity	NPC261607
0.8333	Intermediate Similarity	NPC184463
0.8333	Intermediate Similarity	NPC475925
0.8333	Intermediate Similarity	NPC30515
0.8295	Intermediate Similarity	NPC237540
0.8293	Intermediate Similarity	NPC123360
0.828	Intermediate Similarity	NPC169205
0.8276	Intermediate Similarity	NPC78089
0.8276	Intermediate Similarity	NPC21469
0.8272	Intermediate Similarity	NPC114727
0.8272	Intermediate Similarity	NPC476590
0.8272	Intermediate Similarity	NPC140287
0.8261	Intermediate Similarity	NPC475659
0.825	Intermediate Similarity	NPC163003
0.8242	Intermediate Similarity	NPC179746
0.8242	Intermediate Similarity	NPC81419
0.8242	Intermediate Similarity	NPC212486
0.8242	Intermediate Similarity	NPC476300
0.8235	Intermediate Similarity	NPC471325
0.8222	Intermediate Similarity	NPC51004
0.8222	Intermediate Similarity	NPC474761
0.8222	Intermediate Similarity	NPC476004
0.8214	Intermediate Similarity	NPC19841
0.8214	Intermediate Similarity	NPC178277
0.8211	Intermediate Similarity	NPC185141
0.8211	Intermediate Similarity	NPC133907
0.8211	Intermediate Similarity	NPC164598
0.8211	Intermediate Similarity	NPC474339
0.8211	Intermediate Similarity	NPC46998
0.8211	Intermediate Similarity	NPC128733
0.8211	Intermediate Similarity	NPC110443
0.8211	Intermediate Similarity	NPC150923
0.8202	Intermediate Similarity	NPC260343
0.8193	Intermediate Similarity	NPC474760
0.8193	Intermediate Similarity	NPC41780
0.8193	Intermediate Similarity	NPC65603
0.8193	Intermediate Similarity	NPC187568
0.8191	Intermediate Similarity	NPC474213
0.8191	Intermediate Similarity	NPC471144
0.8182	Intermediate Similarity	NPC284902
0.8172	Intermediate Similarity	NPC185553
0.8161	Intermediate Similarity	NPC159635
0.8161	Intermediate Similarity	NPC295799
0.8161	Intermediate Similarity	NPC165287
0.8152	Intermediate Similarity	NPC473316
0.8152	Intermediate Similarity	NPC473330
0.8152	Intermediate Similarity	NPC323008
0.8152	Intermediate Similarity	NPC167219
0.8152	Intermediate Similarity	NPC470013
0.8152	Intermediate Similarity	NPC469632
0.8152	Intermediate Similarity	NPC470010
0.8152	Intermediate Similarity	NPC262133
0.8152	Intermediate Similarity	NPC198853
0.8152	Intermediate Similarity	NPC140543
0.814	Intermediate Similarity	NPC474252
0.814	Intermediate Similarity	NPC173609
0.814	Intermediate Similarity	NPC474291
0.8132	Intermediate Similarity	NPC12172
0.8132	Intermediate Similarity	NPC133698
0.8132	Intermediate Similarity	NPC208886
0.8132	Intermediate Similarity	NPC131209
0.8125	Intermediate Similarity	NPC140591
0.8125	Intermediate Similarity	NPC149371
0.8125	Intermediate Similarity	NPC291500
0.8125	Intermediate Similarity	NPC86077
0.8125	Intermediate Similarity	NPC303653
0.8125	Intermediate Similarity	NPC189609
0.8125	Intermediate Similarity	NPC197835
0.8125	Intermediate Similarity	NPC471148
0.8111	Intermediate Similarity	NPC307411
0.8111	Intermediate Similarity	NPC151770
0.8111	Intermediate Similarity	NPC212598
0.8095	Intermediate Similarity	NPC128276

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 NPC475461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1590
0.2-0.3	3629
0.3-0.4	2492
0.4-0.5	809
0.5-0.6	335
0.6-0.7	96
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7154	Phase 3
0.7826	Intermediate Similarity	NPD6698	Approved
0.7826	Intermediate Similarity	NPD5785	Approved
0.7826	Intermediate Similarity	NPD46	Approved
0.7667	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5363	Approved
0.7629	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7838	Discovery
0.7444	Intermediate Similarity	NPD5362	Discontinued
0.7404	Intermediate Similarity	NPD6371	Approved
0.734	Intermediate Similarity	NPD1695	Approved
0.7333	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4270	Approved
0.7303	Intermediate Similarity	NPD4820	Approved
0.7303	Intermediate Similarity	NPD4822	Approved
0.7303	Intermediate Similarity	NPD4821	Approved
0.7303	Intermediate Similarity	NPD4819	Approved
0.7283	Intermediate Similarity	NPD1694	Approved
0.7283	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4271	Approved
0.7273	Intermediate Similarity	NPD4268	Approved
0.7204	Intermediate Similarity	NPD5786	Approved
0.7204	Intermediate Similarity	NPD4249	Approved
0.7188	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD6435	Approved
0.7128	Intermediate Similarity	NPD4250	Approved
0.7128	Intermediate Similarity	NPD4251	Approved
0.7113	Intermediate Similarity	NPD5778	Approved
0.7113	Intermediate Similarity	NPD5779	Approved
0.7111	Intermediate Similarity	NPD4252	Approved
0.71	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6686	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5368	Approved
0.6882	Remote Similarity	NPD5332	Approved
0.6882	Remote Similarity	NPD5331	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD7640	Approved
0.6848	Remote Similarity	NPD4790	Discontinued
0.6847	Remote Similarity	NPD7115	Discovery
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6796	Remote Similarity	NPD5344	Discontinued
0.6789	Remote Similarity	NPD6053	Discontinued
0.6778	Remote Similarity	NPD4756	Discovery
0.6774	Remote Similarity	NPD5209	Approved
0.6768	Remote Similarity	NPD6399	Phase 3
0.6765	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD6411	Approved
0.6633	Remote Similarity	NPD5370	Suspended
0.6556	Remote Similarity	NPD8039	Approved
0.6538	Remote Similarity	NPD6648	Approved
0.6505	Remote Similarity	NPD6083	Phase 2
0.6505	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6442	Remote Similarity	NPD5696	Approved
0.6422	Remote Similarity	NPD6899	Approved
0.6422	Remote Similarity	NPD6881	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6389	Remote Similarity	NPD6402	Approved
0.6389	Remote Similarity	NPD5739	Approved
0.6389	Remote Similarity	NPD6675	Approved
0.6389	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6337	Remote Similarity	NPD7515	Phase 2
0.633	Remote Similarity	NPD5701	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD3618	Phase 1
0.6327	Remote Similarity	NPD6684	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6325	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6306	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD7290	Approved
0.6306	Remote Similarity	NPD7102	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3665	Phase 1
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3666	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD7320	Approved
0.6262	Remote Similarity	NPD5211	Phase 2
0.6262	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4695	Discontinued
0.6207	Remote Similarity	NPD7331	Phase 2
0.6204	Remote Similarity	NPD6647	Phase 2
0.62	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.62	Remote Similarity	NPD6903	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5284	Approved
0.6176	Remote Similarity	NPD5693	Phase 1
0.6176	Remote Similarity	NPD5281	Approved
0.6163	Remote Similarity	NPD3197	Phase 1
0.6162	Remote Similarity	NPD5279	Phase 3
0.6162	Remote Similarity	NPD6422	Discontinued
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6147	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD4753	Phase 2
0.6136	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4786	Approved
0.6106	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7341	Phase 2
0.6091	Remote Similarity	NPD6008	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.6075	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD5286	Approved
0.6066	Remote Similarity	NPD8074	Phase 3
0.6047	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4755	Approved
0.6036	Remote Similarity	NPD6412	Phase 2
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6274	Approved
0.6023	Remote Similarity	NPD3704	Approved
0.602	Remote Similarity	NPD6695	Phase 3
0.602	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD8035	Phase 2
0.6018	Remote Similarity	NPD2067	Discontinued
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4623	Approved
0.5984	Remote Similarity	NPD7507	Approved
0.5983	Remote Similarity	NPD7505	Discontinued
0.598	Remote Similarity	NPD5328	Approved
0.5965	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.5963	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD4202	Approved
0.595	Remote Similarity	NPD7642	Approved
0.595	Remote Similarity	NPD7829	Approved
0.595	Remote Similarity	NPD7830	Approved
0.5943	Remote Similarity	NPD5222	Approved
0.5943	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5221	Approved
0.5943	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7641	Discontinued
0.593	Remote Similarity	NPD368	Approved
0.5926	Remote Similarity	NPD4700	Approved
0.5926	Remote Similarity	NPD3172	Approved
0.5922	Remote Similarity	NPD5207	Approved
0.5918	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD5175	Approved
0.59	Remote Similarity	NPD1696	Phase 3
0.5891	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5173	Approved
0.5882	Remote Similarity	NPD7101	Approved
0.5882	Remote Similarity	NPD7100	Approved
0.5877	Remote Similarity	NPD6420	Discontinued
0.5876	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7260	Phase 2
0.5872	Remote Similarity	NPD5223	Approved
0.5862	Remote Similarity	NPD4632	Approved
0.5854	Remote Similarity	NPD4266	Approved
0.5854	Remote Similarity	NPD8273	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