NPASS Compound

Structure

NPC329952 OpenBabel07101718292D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.3383 -0.7383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7274 -3.6266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3159 0.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3159 0.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6069 -2.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2965 -1.6350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2211 -1.0144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2965 -1.6350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7284 -1.5308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0748 -2.2194 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0748 -2.2194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2211 -1.0144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0259 -1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6069 -2.6339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8978 -2.7875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1561 -0.6598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 -0.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6202 -1.8632 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 2 0 0 0 0 2 14 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 6 1 6 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 6 0 0 0 17 25 1 0 0 0 0 18 22 1 1 0 0 0 18 27 1 0 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 3 1 6 0 0 0 20 28 1 0 0 0 0 21 4 1 1 0 0 0 21 29 1 0 0 0 0 22 5 1 1 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.21
Volume:	414.385
LogP:	2.0
LogD:	1.351
LogS:	-3.443
# Rotatable Bonds:	2
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	6.24
Fsp3:	0.773
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:	-4.78
MDCK Permeability:	2.9690638257307e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.673
Plasma Protein Binding (PPB):	73.75214385986328%
Volume Distribution (VD):	0.911
Pgp-substrate:	26.165815353393555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.652
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	5.618
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.56
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.611
Carcinogencity:	0.847
Eye Corrosion:	0.015
Eye Irritation:	0.063
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC329952

Natural Product ID:	NPC329952
*Common Name:**	Querciformolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JSILRCIAUYHSMM-ZVNQDOHQSA-N
Standard InCHI:	InChI=1S/C22H32O7/c1-13-15-6-9-20(3,28-19(13)26)16(24)7-10-22(5)18(27-14(2)23)8-11-21(4,29-22)17(25)12-15/h15,17-18,25H,1,6-12H2,2-5H3/t15-,17+,18+,20-,21-,22-/m1/s1
SMILES:	CC(=O)OC1CCC2(C(CC3CCC(C(=O)CCC1(O2)C)(OC(=O)C3=C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490421
PubChem CID:	25137619
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	4

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[455003]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[455003]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[455003]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[455003]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[455003]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[455003]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[455003]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<	20.0	ug ml-1	PMID[455003]

☑ 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 NPC329952 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	1773
0.2-0.3	5678
0.3-0.4	10663
0.4-0.5	12748
0.5-0.6	7801
0.6-0.7	3409
0.7-0.8	381
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC173926
0.931	High Similarity	NPC474951
0.8966	High Similarity	NPC474949
0.8966	High Similarity	NPC475019
0.8851	High Similarity	NPC329749
0.875	High Similarity	NPC476015
0.875	High Similarity	NPC474762
0.8696	High Similarity	NPC190294
0.8652	High Similarity	NPC248602
0.8617	High Similarity	NPC328562
0.8617	High Similarity	NPC323421
0.8602	High Similarity	NPC475900
0.8556	High Similarity	NPC58219
0.8556	High Similarity	NPC177629
0.8523	High Similarity	NPC474780
0.8511	High Similarity	NPC470883
0.8511	High Similarity	NPC158416
0.8511	High Similarity	NPC476009
0.8511	High Similarity	NPC31645
0.8511	High Similarity	NPC39859
0.8511	High Similarity	NPC76862
0.8462	Intermediate Similarity	NPC92974
0.8444	Intermediate Similarity	NPC186148
0.8427	Intermediate Similarity	NPC47958
0.8427	Intermediate Similarity	NPC304509
0.8427	Intermediate Similarity	NPC149725
0.8352	Intermediate Similarity	NPC153805
0.8352	Intermediate Similarity	NPC474471
0.8352	Intermediate Similarity	NPC227379
0.8352	Intermediate Similarity	NPC281516
0.8315	Intermediate Similarity	NPC9868
0.8315	Intermediate Similarity	NPC3464
0.8315	Intermediate Similarity	NPC151176
0.8315	Intermediate Similarity	NPC475963
0.828	Intermediate Similarity	NPC30515
0.828	Intermediate Similarity	NPC184463
0.8276	Intermediate Similarity	NPC474981
0.8265	Intermediate Similarity	NPC320019
0.8265	Intermediate Similarity	NPC324017
0.8261	Intermediate Similarity	NPC307411
0.8211	Intermediate Similarity	NPC322188
0.8202	Intermediate Similarity	NPC11620
0.8202	Intermediate Similarity	NPC474472
0.8202	Intermediate Similarity	NPC257358
0.8172	Intermediate Similarity	NPC51004
0.8163	Intermediate Similarity	NPC476270
0.8163	Intermediate Similarity	NPC15993
0.8152	Intermediate Similarity	NPC202672
0.8105	Intermediate Similarity	NPC71589
0.8085	Intermediate Similarity	NPC12172
0.8085	Intermediate Similarity	NPC208886
0.8081	Intermediate Similarity	NPC474747
0.8041	Intermediate Similarity	NPC40812
0.8022	Intermediate Similarity	NPC137033
0.8021	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC212486
0.8	Intermediate Similarity	NPC472747
0.8	Intermediate Similarity	NPC475912
0.8	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC472750
0.8	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC81419
0.798	Intermediate Similarity	NPC201718
0.7979	Intermediate Similarity	NPC476004
0.7979	Intermediate Similarity	NPC474761
0.7979	Intermediate Similarity	NPC65359
0.7959	Intermediate Similarity	NPC187761
0.7959	Intermediate Similarity	NPC83895
0.7935	Intermediate Similarity	NPC470242
0.7921	Intermediate Similarity	NPC472748
0.7917	Intermediate Similarity	NPC474035
0.7917	Intermediate Similarity	NPC81386
0.7912	Intermediate Similarity	NPC70424
0.7912	Intermediate Similarity	NPC243618
0.7912	Intermediate Similarity	NPC72464
0.7895	Intermediate Similarity	NPC475881
0.7895	Intermediate Similarity	NPC70251
0.7895	Intermediate Similarity	NPC470373
0.7895	Intermediate Similarity	NPC469627
0.7895	Intermediate Similarity	NPC470379
0.7865	Intermediate Similarity	NPC233377
0.7857	Intermediate Similarity	NPC474313
0.7857	Intermediate Similarity	NPC471150
0.7849	Intermediate Similarity	NPC190753
0.7849	Intermediate Similarity	NPC118601
0.7843	Intermediate Similarity	NPC472751
0.7843	Intermediate Similarity	NPC472749
0.7835	Intermediate Similarity	NPC14961
0.7835	Intermediate Similarity	NPC270013
0.7835	Intermediate Similarity	NPC163228
0.7822	Intermediate Similarity	NPC473148
0.7822	Intermediate Similarity	NPC472755
0.7802	Intermediate Similarity	NPC128429
0.78	Intermediate Similarity	NPC474742
0.78	Intermediate Similarity	NPC472753
0.78	Intermediate Similarity	NPC47880
0.7789	Intermediate Similarity	NPC206614
0.7789	Intermediate Similarity	NPC474323
0.7778	Intermediate Similarity	NPC261377
0.7778	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC308567
0.7766	Intermediate Similarity	NPC178875
0.7755	Intermediate Similarity	NPC476315
0.7745	Intermediate Similarity	NPC474741
0.7742	Intermediate Similarity	NPC164393
0.7723	Intermediate Similarity	NPC472754
0.7723	Intermediate Similarity	NPC149371
0.7667	Intermediate Similarity	NPC103634
0.766	Intermediate Similarity	NPC179659
0.766	Intermediate Similarity	NPC5130
0.7647	Intermediate Similarity	NPC475873
0.7624	Intermediate Similarity	NPC474339
0.7624	Intermediate Similarity	NPC164598
0.7624	Intermediate Similarity	NPC46998
0.7624	Intermediate Similarity	NPC185141
0.7624	Intermediate Similarity	NPC128733
0.7624	Intermediate Similarity	NPC110443
0.7624	Intermediate Similarity	NPC133907
0.7619	Intermediate Similarity	NPC38154
0.7604	Intermediate Similarity	NPC329857
0.7604	Intermediate Similarity	NPC316228
0.7604	Intermediate Similarity	NPC246173
0.7604	Intermediate Similarity	NPC469718
0.76	Intermediate Similarity	NPC471144
0.76	Intermediate Similarity	NPC474213
0.76	Intermediate Similarity	NPC300584
0.7596	Intermediate Similarity	NPC477513
0.7573	Intermediate Similarity	NPC472756
0.7573	Intermediate Similarity	NPC100487
0.7551	Intermediate Similarity	NPC473331
0.7549	Intermediate Similarity	NPC80144
0.7549	Intermediate Similarity	NPC106668
0.7549	Intermediate Similarity	NPC471148
0.7549	Intermediate Similarity	NPC225353
0.7528	Intermediate Similarity	NPC122847
0.7526	Intermediate Similarity	NPC20713
0.7525	Intermediate Similarity	NPC475949
0.7525	Intermediate Similarity	NPC471381
0.7525	Intermediate Similarity	NPC186861
0.75	Intermediate Similarity	NPC474101
0.75	Intermediate Similarity	NPC111348
0.75	Intermediate Similarity	NPC474032
0.75	Intermediate Similarity	NPC474291
0.75	Intermediate Similarity	NPC20066
0.75	Intermediate Similarity	NPC44004
0.7476	Intermediate Similarity	NPC110989
0.7476	Intermediate Similarity	NPC27687
0.7476	Intermediate Similarity	NPC37240
0.7475	Intermediate Similarity	NPC272050
0.7475	Intermediate Similarity	NPC474947
0.7475	Intermediate Similarity	NPC472873
0.7474	Intermediate Similarity	NPC231889
0.7455	Intermediate Similarity	NPC471146
0.7455	Intermediate Similarity	NPC471145
0.7451	Intermediate Similarity	NPC67296
0.7449	Intermediate Similarity	NPC135776
0.7449	Intermediate Similarity	NPC61275
0.7449	Intermediate Similarity	NPC153590
0.7449	Intermediate Similarity	NPC475788
0.7449	Intermediate Similarity	NPC273579
0.7449	Intermediate Similarity	NPC288240
0.7449	Intermediate Similarity	NPC162205
0.7449	Intermediate Similarity	NPC295204
0.7447	Intermediate Similarity	NPC21469
0.7447	Intermediate Similarity	NPC99395
0.7447	Intermediate Similarity	NPC197903
0.7429	Intermediate Similarity	NPC148270
0.7429	Intermediate Similarity	NPC197813
0.7429	Intermediate Similarity	NPC80338
0.7426	Intermediate Similarity	NPC17183
0.7426	Intermediate Similarity	NPC161855
0.7426	Intermediate Similarity	NPC249171
0.7426	Intermediate Similarity	NPC472015
0.7426	Intermediate Similarity	NPC473326
0.7426	Intermediate Similarity	NPC49833
0.7423	Intermediate Similarity	NPC473619
0.7423	Intermediate Similarity	NPC473448
0.7423	Intermediate Similarity	NPC475748
0.7404	Intermediate Similarity	NPC203659
0.74	Intermediate Similarity	NPC91771
0.74	Intermediate Similarity	NPC473859
0.74	Intermediate Similarity	NPC142529
0.74	Intermediate Similarity	NPC473291
0.74	Intermediate Similarity	NPC260223
0.7396	Intermediate Similarity	NPC207114
0.7396	Intermediate Similarity	NPC217983
0.7391	Intermediate Similarity	NPC47635
0.7383	Intermediate Similarity	NPC100908
0.7383	Intermediate Similarity	NPC5103
0.7379	Intermediate Similarity	NPC35185
0.7379	Intermediate Similarity	NPC4899
0.7379	Intermediate Similarity	NPC177013
0.7379	Intermediate Similarity	NPC473596
0.7379	Intermediate Similarity	NPC474730
0.7374	Intermediate Similarity	NPC303942
0.7374	Intermediate Similarity	NPC57405
0.7374	Intermediate Similarity	NPC476722
0.7374	Intermediate Similarity	NPC121825

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 NPC329952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	2388
0.2-0.3	3687
0.3-0.4	1840
0.4-0.5	653
0.5-0.6	281
0.6-0.7	58
0.7-0.8	3
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
0.7604	Intermediate Similarity	NPD46	Approved
0.7604	Intermediate Similarity	NPD6698	Approved
0.7358	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7838	Discovery
0.6881	Remote Similarity	NPD6686	Approved
0.6796	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6110	Phase 1
0.6637	Remote Similarity	NPD6053	Discontinued
0.661	Remote Similarity	NPD6921	Approved
0.6579	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD5282	Discontinued
0.6525	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD8328	Phase 3
0.6491	Remote Similarity	NPD8297	Approved
0.6481	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD1695	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6009	Approved
0.6406	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD7642	Approved
0.6364	Remote Similarity	NPD7604	Phase 2
0.6356	Remote Similarity	NPD7641	Discontinued
0.6339	Remote Similarity	NPD5697	Approved
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8269	Approved
0.6333	Remote Similarity	NPD8268	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8266	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8513	Phase 3
0.6333	Remote Similarity	NPD8267	Approved
0.6333	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7320	Approved
0.6283	Remote Similarity	NPD6011	Approved
0.6281	Remote Similarity	NPD8080	Discontinued
0.6271	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7260	Phase 2
0.6262	Remote Similarity	NPD7839	Suspended
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD7507	Approved
0.626	Remote Similarity	NPD6336	Discontinued
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD5785	Approved
0.6228	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6228	Remote Similarity	NPD6012	Approved
0.6224	Remote Similarity	NPD5368	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6207	Remote Similarity	NPD6882	Approved
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD6084	Phase 2
0.6198	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6412	Phase 2
0.6195	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD6411	Approved
0.618	Remote Similarity	NPD7909	Approved
0.6176	Remote Similarity	NPD5786	Approved
0.6162	Remote Similarity	NPD5369	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD4225	Approved
0.6147	Remote Similarity	NPD7638	Approved
0.6134	Remote Similarity	NPD7115	Discovery
0.6129	Remote Similarity	NPD8451	Approved
0.6121	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6059	Approved
0.6111	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD7341	Phase 2
0.61	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7829	Approved
0.6098	Remote Similarity	NPD7830	Approved
0.6094	Remote Similarity	NPD6845	Suspended
0.6091	Remote Similarity	NPD6648	Approved
0.6091	Remote Similarity	NPD7639	Approved
0.6091	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8448	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.608	Remote Similarity	NPD8074	Phase 3
0.6078	Remote Similarity	NPD5363	Approved
0.6078	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD8444	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6044	Remote Similarity	NPD7331	Phase 2
0.604	Remote Similarity	NPD7154	Phase 3
0.6034	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5695	Phase 3
0.6016	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD3197	Phase 1
0.5982	Remote Similarity	NPD8083	Approved
0.5982	Remote Similarity	NPD8086	Approved
0.5982	Remote Similarity	NPD8084	Approved
0.5982	Remote Similarity	NPD8138	Approved
0.5982	Remote Similarity	NPD8082	Approved
0.5982	Remote Similarity	NPD8085	Approved
0.5982	Remote Similarity	NPD8139	Approved
0.5981	Remote Similarity	NPD6399	Phase 3
0.595	Remote Similarity	NPD6335	Approved
0.5941	Remote Similarity	NPD4270	Approved
0.5941	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4269	Approved
0.5938	Remote Similarity	NPD8390	Approved
0.5938	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD8392	Approved
0.5929	Remote Similarity	NPD8275	Approved
0.5929	Remote Similarity	NPD8276	Approved
0.5922	Remote Similarity	NPD1694	Approved
0.592	Remote Similarity	NPD8341	Approved
0.592	Remote Similarity	NPD8342	Approved
0.592	Remote Similarity	NPD8299	Approved
0.592	Remote Similarity	NPD8340	Approved
0.5918	Remote Similarity	NPD4756	Discovery
0.5917	Remote Similarity	NPD6274	Approved
0.5909	Remote Similarity	NPD7902	Approved
0.5905	Remote Similarity	NPD6672	Approved
0.5905	Remote Similarity	NPD5737	Approved
0.5902	Remote Similarity	NPD7100	Approved
0.5902	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD4634	Approved
0.5888	Remote Similarity	NPD8035	Phase 2
0.5888	Remote Similarity	NPD5693	Phase 1
0.5888	Remote Similarity	NPD8034	Phase 2
0.5882	Remote Similarity	NPD5362	Discontinued
0.5877	Remote Similarity	NPD8081	Approved
0.5868	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6317	Approved
0.5865	Remote Similarity	NPD6422	Discontinued
0.5859	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4802	Phase 2
0.5859	Remote Similarity	NPD4238	Approved
0.5842	Remote Similarity	NPD1779	Approved
0.5842	Remote Similarity	NPD1780	Approved
0.5841	Remote Similarity	NPD5211	Phase 2
0.5826	Remote Similarity	NPD8393	Approved
0.5826	Remote Similarity	NPD6008	Approved
0.582	Remote Similarity	NPD6313	Approved
0.582	Remote Similarity	NPD6314	Approved
0.581	Remote Similarity	NPD4250	Approved
0.581	Remote Similarity	NPD4251	Approved
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5785	Remote Similarity	NPD6868	Approved
0.5781	Remote Similarity	NPD6033	Approved
0.578	Remote Similarity	NPD7748	Approved
0.5776	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4755	Approved
0.5752	Remote Similarity	NPD5223	Approved
0.5743	Remote Similarity	NPD4821	Approved
0.5743	Remote Similarity	NPD4822	Approved
0.5743	Remote Similarity	NPD4820	Approved
0.5743	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4819	Approved
0.5743	Remote Similarity	NPD4252	Approved
0.5741	Remote Similarity	NPD7515	Phase 2
0.5739	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5141	Approved
0.5739	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3669	Approved
0.5728	Remote Similarity	NPD4788	Approved
0.5728	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4249	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	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