NPASS Compound

Structure

NPC476015 OpenBabel07101719252D 32 34 0 0 1 0 0 0 0 0999 V2000 0.5215 1.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4401 -2.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1410 1.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4244 -1.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8454 0.3964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3649 1.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4669 1.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3153 -0.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7778 -1.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7922 0.7129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4471 0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3910 1.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4770 0.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5741 -1.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 2.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9668 1.4787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7018 -0.7124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7081 -0.4100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8534 1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5844 0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2019 -1.0011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8783 0.1418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4606 0.8876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7081 -2.4100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2704 2.8886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7581 -0.3245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4688 -1.6813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5741 -0.9100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2901 2.1371 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 2.2080 -0.1212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 25 2 0 0 0 0 15 29 1 0 0 0 0 16 26 2 0 0 0 0 16 30 1 0 0 0 0 17 7 1 1 0 0 0 18 22 1 1 0 0 0 18 31 1 0 0 0 0 19 23 1 6 0 0 0 19 29 1 0 0 0 0 20 24 1 1 0 0 0 20 30 1 0 0 0 0 21 27 2 0 0 0 0 21 32 1 0 0 0 0 22 4 1 6 0 0 0 22 28 1 0 0 0 0 23 5 1 1 0 0 0 23 32 1 0 0 0 0 24 6 1 6 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.24
Volume:	457.767
LogP:	2.501
LogD:	1.335
LogS:	-3.994
# Rotatable Bonds:	4
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	6.241
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.792
MDCK Permeability:	3.937525980290957e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.756
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	77.27986907958984%
Volume Distribution (VD):	1.287
Pgp-substrate:	26.971641540527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	3.179
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.276
Skin Sensitization:	0.955
Carcinogencity:	0.277
Eye Corrosion:	0.165
Eye Irritation:	0.367
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC476015

Natural Product ID:	NPC476015
*Common Name:**	Querciformolide C
IUPAC Name:	n.a.
Synonyms:	Querciformolide C
Standard InCHIKey:	XEMHTBDOSSDMLI-UEMXEBGWSA-N
Standard InCHI:	InChI=1S/C24H36O8/c1-14-17-7-11-23(5,32-21(14)27)19(29-15(2)25)8-10-22(4,28)18-9-12-24(6,31-18)20(13-17)30-16(3)26/h17-20,28H,1,7-13H2,2-6H3/t17-,18+,19-,20+,22-,23-,24-/m1/s1
SMILES:	CC(=O)OC1CCC(C2CCC(O2)(C(CC3CCC1(OC(=O)C3=C)C)OC(=O)C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521633
PubChem CID:	25137620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18831569]
NPO7475	Sinularia querciformis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18831569]
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672798]
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7475	Sinularia querciformis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	4
IC50	3
Others	1

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[472778]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[472778]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[472778]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[472778]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[472778]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	23.7	%	PMID[472778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[472778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<	20.0	ug ml-1	PMID[472778]

☑ 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 NPC476015 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1725
0.2-0.3	6039
0.3-0.4	13767
0.4-0.5	10230
0.5-0.6	7381
0.6-0.7	2585
0.7-0.8	643
0.8-0.85	67
0.85-0.9	23
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474762
0.9753	High Similarity	NPC474949
0.9753	High Similarity	NPC475019
0.963	High Similarity	NPC329749
0.939	High Similarity	NPC149725
0.939	High Similarity	NPC47958
0.939	High Similarity	NPC304509
0.9268	High Similarity	NPC474780
0.9268	High Similarity	NPC3464
0.9268	High Similarity	NPC151176
0.9268	High Similarity	NPC475963
0.925	High Similarity	NPC474981
0.9176	High Similarity	NPC92974
0.9176	High Similarity	NPC474951
0.9146	High Similarity	NPC474472
0.9146	High Similarity	NPC257358
0.9059	High Similarity	NPC177629
0.9059	High Similarity	NPC58219
0.8953	High Similarity	NPC307411
0.8953	High Similarity	NPC173926
0.8941	High Similarity	NPC248602
0.8941	High Similarity	NPC186148
0.8864	High Similarity	NPC476300
0.8851	High Similarity	NPC51004
0.875	High Similarity	NPC184463
0.875	High Similarity	NPC30515
0.875	High Similarity	NPC329952
0.8667	High Similarity	NPC475900
0.8667	High Similarity	NPC36954
0.8636	High Similarity	NPC476004
0.8636	High Similarity	NPC474761
0.8621	High Similarity	NPC202672
0.8621	High Similarity	NPC281516
0.8621	High Similarity	NPC227379
0.8621	High Similarity	NPC153805
0.8621	High Similarity	NPC474471
0.8571	High Similarity	NPC470883
0.8571	High Similarity	NPC31645
0.8571	High Similarity	NPC39859
0.8571	High Similarity	NPC476009
0.8571	High Similarity	NPC158416
0.8571	High Similarity	NPC76862
0.8556	High Similarity	NPC190294
0.8539	High Similarity	NPC12172
0.8539	High Similarity	NPC208886
0.8506	High Similarity	NPC190753
0.8478	Intermediate Similarity	NPC328562
0.8478	Intermediate Similarity	NPC323421
0.8471	Intermediate Similarity	NPC11620
0.8444	Intermediate Similarity	NPC179746
0.8444	Intermediate Similarity	NPC81419
0.8444	Intermediate Similarity	NPC212486
0.8444	Intermediate Similarity	NPC475912
0.8391	Intermediate Similarity	NPC470242
0.837	Intermediate Similarity	NPC476315
0.8352	Intermediate Similarity	NPC474035
0.8352	Intermediate Similarity	NPC81386
0.8333	Intermediate Similarity	NPC475881
0.8333	Intermediate Similarity	NPC70251
0.8295	Intermediate Similarity	NPC5130
0.8295	Intermediate Similarity	NPC118601
0.828	Intermediate Similarity	NPC471150
0.8276	Intermediate Similarity	NPC137033
0.8261	Intermediate Similarity	NPC270013
0.8261	Intermediate Similarity	NPC14961
0.8222	Intermediate Similarity	NPC475748
0.8222	Intermediate Similarity	NPC474323
0.8222	Intermediate Similarity	NPC206614
0.8211	Intermediate Similarity	NPC15993
0.8202	Intermediate Similarity	NPC178875
0.8161	Intermediate Similarity	NPC9868
0.8125	Intermediate Similarity	NPC324017
0.8125	Intermediate Similarity	NPC320019
0.8105	Intermediate Similarity	NPC186861
0.809	Intermediate Similarity	NPC231889
0.8021	Intermediate Similarity	NPC47880
0.8	Intermediate Similarity	NPC474213
0.7978	Intermediate Similarity	NPC162071
0.7978	Intermediate Similarity	NPC164393
0.7955	Intermediate Similarity	NPC72464
0.7938	Intermediate Similarity	NPC474747
0.7938	Intermediate Similarity	NPC149371
0.7917	Intermediate Similarity	NPC471381
0.7912	Intermediate Similarity	NPC474032
0.7912	Intermediate Similarity	NPC151770
0.7907	Intermediate Similarity	NPC233377
0.7895	Intermediate Similarity	NPC474313
0.7895	Intermediate Similarity	NPC40812
0.7879	Intermediate Similarity	NPC223450
0.7872	Intermediate Similarity	NPC476053
0.7872	Intermediate Similarity	NPC475659
0.7872	Intermediate Similarity	NPC472873
0.7872	Intermediate Similarity	NPC163228
0.7865	Intermediate Similarity	NPC21469
0.7865	Intermediate Similarity	NPC197903
0.7865	Intermediate Similarity	NPC99395
0.7857	Intermediate Similarity	NPC475871
0.7857	Intermediate Similarity	NPC475945
0.7857	Intermediate Similarity	NPC472755
0.7849	Intermediate Similarity	NPC135776
0.7849	Intermediate Similarity	NPC153590
0.7841	Intermediate Similarity	NPC272814
0.7835	Intermediate Similarity	NPC474742
0.7835	Intermediate Similarity	NPC476270
0.7826	Intermediate Similarity	NPC473619
0.7826	Intermediate Similarity	NPC473448
0.7826	Intermediate Similarity	NPC65359
0.7812	Intermediate Similarity	NPC473326
0.7812	Intermediate Similarity	NPC471144
0.7802	Intermediate Similarity	NPC207114
0.7802	Intermediate Similarity	NPC79549
0.7802	Intermediate Similarity	NPC89001
0.7802	Intermediate Similarity	NPC217983
0.7791	Intermediate Similarity	NPC19841
0.7789	Intermediate Similarity	NPC473859
0.7789	Intermediate Similarity	NPC279621
0.7778	Intermediate Similarity	NPC474741
0.7778	Intermediate Similarity	NPC100487
0.7766	Intermediate Similarity	NPC57405
0.7766	Intermediate Similarity	NPC71589
0.7766	Intermediate Similarity	NPC303942
0.7755	Intermediate Similarity	NPC225353
0.7755	Intermediate Similarity	NPC80144
0.7755	Intermediate Similarity	NPC472754
0.7753	Intermediate Similarity	NPC138647
0.7753	Intermediate Similarity	NPC470238
0.7753	Intermediate Similarity	NPC70424
0.7753	Intermediate Similarity	NPC243618
0.7742	Intermediate Similarity	NPC470379
0.7742	Intermediate Similarity	NPC470373
0.7742	Intermediate Similarity	NPC133698
0.7742	Intermediate Similarity	NPC184063
0.7742	Intermediate Similarity	NPC473321
0.7738	Intermediate Similarity	NPC217725
0.7732	Intermediate Similarity	NPC288876
0.7727	Intermediate Similarity	NPC103171
0.7727	Intermediate Similarity	NPC474291
0.7727	Intermediate Similarity	NPC246076
0.7717	Intermediate Similarity	NPC215556
0.7717	Intermediate Similarity	NPC295312
0.7717	Intermediate Similarity	NPC477017
0.7717	Intermediate Similarity	NPC477016
0.7717	Intermediate Similarity	NPC477011
0.7708	Intermediate Similarity	NPC181151
0.77	Intermediate Similarity	NPC243998
0.77	Intermediate Similarity	NPC54737
0.7684	Intermediate Similarity	NPC471142
0.7684	Intermediate Similarity	NPC471141
0.7677	Intermediate Similarity	NPC475873
0.7677	Intermediate Similarity	NPC37240
0.7677	Intermediate Similarity	NPC473148
0.7677	Intermediate Similarity	NPC110989
0.7667	Intermediate Similarity	NPC329615
0.7667	Intermediate Similarity	NPC284534
0.7667	Intermediate Similarity	NPC477018
0.7667	Intermediate Similarity	NPC204105
0.7667	Intermediate Similarity	NPC329838
0.7667	Intermediate Similarity	NPC100921
0.7667	Intermediate Similarity	NPC300082
0.766	Intermediate Similarity	NPC295204
0.766	Intermediate Similarity	NPC308656
0.766	Intermediate Similarity	NPC60386
0.766	Intermediate Similarity	NPC473273
0.766	Intermediate Similarity	NPC473234
0.766	Intermediate Similarity	NPC273579
0.766	Intermediate Similarity	NPC473263
0.766	Intermediate Similarity	NPC288240
0.766	Intermediate Similarity	NPC162205
0.7653	Intermediate Similarity	NPC472753
0.7653	Intermediate Similarity	NPC201718
0.7653	Intermediate Similarity	NPC67296
0.7647	Intermediate Similarity	NPC139838
0.7647	Intermediate Similarity	NPC59489
0.764	Intermediate Similarity	NPC250315
0.764	Intermediate Similarity	NPC128429
0.7634	Intermediate Similarity	NPC54065
0.7634	Intermediate Similarity	NPC297474
0.7634	Intermediate Similarity	NPC216284
0.7634	Intermediate Similarity	NPC19087
0.7629	Intermediate Similarity	NPC83895
0.7629	Intermediate Similarity	NPC249171
0.7629	Intermediate Similarity	NPC187761
0.7629	Intermediate Similarity	NPC308567
0.7629	Intermediate Similarity	NPC261377
0.7629	Intermediate Similarity	NPC255592
0.7629	Intermediate Similarity	NPC187268
0.7629	Intermediate Similarity	NPC45125
0.7629	Intermediate Similarity	NPC49833
0.7624	Intermediate Similarity	NPC477513
0.7624	Intermediate Similarity	NPC26617
0.7614	Intermediate Similarity	NPC47635
0.7609	Intermediate Similarity	NPC473715
0.7609	Intermediate Similarity	NPC476704
0.7604	Intermediate Similarity	NPC91771
0.7604	Intermediate Similarity	NPC142529
0.76	Intermediate Similarity	NPC203659
0.76	Intermediate Similarity	NPC472748
0.7582	Intermediate Similarity	NPC309211
0.7582	Intermediate Similarity	NPC477010
0.7582	Intermediate Similarity	NPC284902

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 NPC476015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	2546
0.2-0.3	3751
0.3-0.4	1751
0.4-0.5	537
0.5-0.6	272
0.6-0.7	29
0.7-0.8	5
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
0.7634	Intermediate Similarity	NPD46	Approved
0.7634	Intermediate Similarity	NPD6698	Approved
0.7624	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7983	Approved
0.7263	Intermediate Similarity	NPD7838	Discovery
0.7075	Intermediate Similarity	NPD6371	Approved
0.7048	Intermediate Similarity	NPD6686	Approved
0.6979	Remote Similarity	NPD1695	Approved
0.697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6053	Discontinued
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6435	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7909	Approved
0.6476	Remote Similarity	NPD5344	Discontinued
0.6466	Remote Similarity	NPD8513	Phase 3
0.6466	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD8517	Approved
0.6466	Remote Similarity	NPD8516	Approved
0.6436	Remote Similarity	NPD5778	Approved
0.6436	Remote Similarity	NPD5779	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6383	Remote Similarity	NPD5368	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7154	Phase 3
0.6325	Remote Similarity	NPD8267	Approved
0.6325	Remote Similarity	NPD8268	Approved
0.6325	Remote Similarity	NPD8266	Approved
0.6325	Remote Similarity	NPD8269	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7638	Approved
0.6286	Remote Similarity	NPD4225	Approved
0.6283	Remote Similarity	NPD4632	Approved
0.6263	Remote Similarity	NPD4251	Approved
0.6263	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6238	Remote Similarity	NPD5785	Approved
0.623	Remote Similarity	NPD7319	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD6648	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6224	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5282	Discontinued
0.6198	Remote Similarity	NPD8074	Phase 3
0.6195	Remote Similarity	NPD8297	Approved
0.6186	Remote Similarity	NPD5362	Discontinued
0.6162	Remote Similarity	NPD5786	Approved
0.6162	Remote Similarity	NPD4249	Approved
0.6146	Remote Similarity	NPD5369	Approved
0.6142	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7341	Phase 2
0.6083	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6083	Remote Similarity	NPD7830	Approved
0.6068	Remote Similarity	NPD7641	Discontinued
0.6061	Remote Similarity	NPD1694	Approved
0.6061	Remote Similarity	NPD5363	Approved
0.605	Remote Similarity	NPD6921	Approved
0.6042	Remote Similarity	NPD4821	Approved
0.6042	Remote Similarity	NPD4820	Approved
0.6042	Remote Similarity	NPD4819	Approved
0.6042	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4822	Approved
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6412	Phase 2
0.6033	Remote Similarity	NPD7492	Approved
0.6023	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7260	Phase 2
0.5984	Remote Similarity	NPD6616	Approved
0.5984	Remote Similarity	NPD8273	Phase 1
0.5984	Remote Similarity	NPD8451	Approved
0.5983	Remote Similarity	NPD7115	Discovery
0.5983	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6009	Approved
0.5982	Remote Similarity	NPD6881	Approved
0.5982	Remote Similarity	NPD6899	Approved
0.5966	Remote Similarity	NPD6054	Approved
0.5965	Remote Similarity	NPD6650	Approved
0.5965	Remote Similarity	NPD6649	Approved
0.5962	Remote Similarity	NPD6399	Phase 3
0.5952	Remote Similarity	NPD6845	Suspended
0.595	Remote Similarity	NPD7604	Phase 2
0.5946	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD6008	Approved
0.5946	Remote Similarity	NPD6675	Approved
0.5946	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD7128	Approved
0.5935	Remote Similarity	NPD8448	Approved
0.5935	Remote Similarity	NPD7078	Approved
0.5929	Remote Similarity	NPD6372	Approved
0.5929	Remote Similarity	NPD6373	Approved
0.5918	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4270	Approved
0.5918	Remote Similarity	NPD4269	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD8444	Approved
0.5913	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5697	Approved
0.5887	Remote Similarity	NPD7736	Approved
0.5877	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD7290	Approved
0.5877	Remote Similarity	NPD7102	Approved
0.5868	Remote Similarity	NPD6370	Approved
0.5868	Remote Similarity	NPD8080	Discontinued
0.5859	Remote Similarity	NPD6110	Phase 1
0.5854	Remote Similarity	NPD3728	Approved
0.5854	Remote Similarity	NPD6336	Discontinued
0.5854	Remote Similarity	NPD3730	Approved
0.5851	Remote Similarity	NPD8039	Approved
0.5842	Remote Similarity	NPD6422	Discontinued
0.5841	Remote Similarity	NPD7320	Approved
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5826	Remote Similarity	NPD8130	Phase 1
0.5826	Remote Similarity	NPD6617	Approved
0.5826	Remote Similarity	NPD6847	Approved
0.5826	Remote Similarity	NPD6869	Approved
0.582	Remote Similarity	NPD8328	Phase 3
0.5818	Remote Similarity	NPD7632	Discontinued
0.5806	Remote Similarity	NPD8293	Discontinued
0.5798	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD7327	Approved
0.5795	Remote Similarity	NPD3197	Phase 1
0.5794	Remote Similarity	NPD8392	Approved
0.5794	Remote Similarity	NPD8391	Approved
0.5794	Remote Similarity	NPD8390	Approved
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6012	Approved
0.5785	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6016	Approved
0.5785	Remote Similarity	NPD6015	Approved
0.5785	Remote Similarity	NPD7503	Approved
0.5772	Remote Similarity	NPD8340	Approved
0.5772	Remote Similarity	NPD8342	Approved
0.5772	Remote Similarity	NPD8299	Approved
0.5772	Remote Similarity	NPD8341	Approved
0.5758	Remote Similarity	NPD5209	Approved
0.5755	Remote Similarity	NPD7748	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.575	Remote Similarity	NPD7516	Approved
0.5743	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD7902	Approved
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6421	Discontinued
0.5738	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4252	Approved
0.5714	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD8294	Approved
0.5702	Remote Similarity	NPD8377	Approved
0.5701	Remote Similarity	NPD5695	Phase 3
0.57	Remote Similarity	NPD4788	Approved
0.57	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5332	Approved
0.57	Remote Similarity	NPD5331	Approved
0.57	Remote Similarity	NPD3669	Approved
0.5698	Remote Similarity	NPD3198	Approved
0.569	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6684	Approved
0.5686	Remote Similarity	NPD5330	Approved
0.5686	Remote Similarity	NPD7521	Approved
0.5686	Remote Similarity	NPD6409	Approved
0.5686	Remote Similarity	NPD7334	Approved
0.5686	Remote Similarity	NPD7146	Approved
0.5676	Remote Similarity	NPD8086	Approved
0.5676	Remote Similarity	NPD8082	Approved
0.5676	Remote Similarity	NPD8139	Approved
0.5676	Remote Similarity	NPD8085	Approved
0.5676	Remote Similarity	NPD8083	Approved
0.5676	Remote Similarity	NPD8138	Approved
0.5676	Remote Similarity	NPD8084	Approved
0.567	Remote Similarity	NPD4238	Approved
0.567	Remote Similarity	NPD4802	Phase 2
0.5663	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4790	Discontinued
0.5657	Remote Similarity	NPD1779	Approved
0.5657	Remote Similarity	NPD1780	Approved
0.5656	Remote Similarity	NPD8380	Approved
0.5656	Remote Similarity	NPD8296	Approved
0.5656	Remote Similarity	NPD8378	Approved
0.5656	Remote Similarity	NPD8379	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