NPASS Compound

Structure

NPC473658 OpenBabel07101718182D 27 28 0 0 1 0 0 0 0 0999 V2000 6.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 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 1.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 15 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 27 1 0 0 0 0 14 2 1 6 0 0 0 14 19 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 20 21 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 4 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	400.088
LogP:	4.306
LogD:	2.927
LogS:	-4.799
# Rotatable Bonds:	9
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	4.314
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71
MDCK Permeability:	2.0897512513329275e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.179

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	92.86353302001953%
Volume Distribution (VD):	2.828
Pgp-substrate:	6.043760299682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	1.633
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.739
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.911
Carcinogencity:	0.929
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC473658

Natural Product ID:	NPC473658
*Common Name:**	Sequoiatone F
IUPAC Name:	methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate
Synonyms:	Sequoiatone F
Standard InCHIKey:	AZRKTTNHSKOLMR-JVEVTSHPSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12+/t14-,22+/m0/s1
SMILES:	CCCCCC[C@@H](C(=O)/C=C/1C(=C2C(=COC(=C2)C)[C@]1(C)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448254
PubChem CID:	15382209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans

*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
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678666]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027772]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15184162]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22103394]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	260.0	uM	PMID[491746]

☑ 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 NPC473658 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	181
0.1-0.2	979
0.2-0.3	4224
0.3-0.4	9032
0.4-0.5	16907
0.5-0.6	7163
0.6-0.7	3514
0.7-0.8	687
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC307092
0.9759	High Similarity	NPC26078
0.9643	High Similarity	NPC51358
0.8434	Intermediate Similarity	NPC316324
0.8	Intermediate Similarity	NPC234038
0.8	Intermediate Similarity	NPC315394
0.7907	Intermediate Similarity	NPC93763
0.7907	Intermediate Similarity	NPC315765
0.7907	Intermediate Similarity	NPC108816
0.7802	Intermediate Similarity	NPC316426
0.7802	Intermediate Similarity	NPC315395
0.7802	Intermediate Similarity	NPC475461
0.7802	Intermediate Similarity	NPC305475
0.7778	Intermediate Similarity	NPC14575
0.7778	Intermediate Similarity	NPC197835
0.7778	Intermediate Similarity	NPC196487
0.7778	Intermediate Similarity	NPC141193
0.7778	Intermediate Similarity	NPC140591
0.7778	Intermediate Similarity	NPC303653
0.7778	Intermediate Similarity	NPC189609
0.7778	Intermediate Similarity	NPC291500
0.7778	Intermediate Similarity	NPC96259
0.7766	Intermediate Similarity	NPC166110
0.7742	Intermediate Similarity	NPC212598
0.7742	Intermediate Similarity	NPC268298
0.7717	Intermediate Similarity	NPC72513
0.7711	Intermediate Similarity	NPC316029
0.7711	Intermediate Similarity	NPC315597
0.7711	Intermediate Similarity	NPC315285
0.7708	Intermediate Similarity	NPC91408
0.7701	Intermediate Similarity	NPC267231
0.7692	Intermediate Similarity	NPC255307
0.7692	Intermediate Similarity	NPC165162
0.7684	Intermediate Similarity	NPC248193
0.7677	Intermediate Similarity	NPC469851
0.767	Intermediate Similarity	NPC228477
0.767	Intermediate Similarity	NPC137911
0.7667	Intermediate Similarity	NPC40746
0.7667	Intermediate Similarity	NPC169575
0.7667	Intermediate Similarity	NPC16488
0.766	Intermediate Similarity	NPC166554
0.766	Intermediate Similarity	NPC129419
0.766	Intermediate Similarity	NPC179394
0.766	Intermediate Similarity	NPC144133
0.766	Intermediate Similarity	NPC265856
0.764	Intermediate Similarity	NPC325031
0.7634	Intermediate Similarity	NPC260343
0.7609	Intermediate Similarity	NPC116575
0.7609	Intermediate Similarity	NPC122502
0.7604	Intermediate Similarity	NPC477131
0.7604	Intermediate Similarity	NPC470013
0.7604	Intermediate Similarity	NPC323008
0.7604	Intermediate Similarity	NPC53685
0.7604	Intermediate Similarity	NPC198853
0.7604	Intermediate Similarity	NPC262133
0.7604	Intermediate Similarity	NPC470010
0.7586	Intermediate Similarity	NPC116177
0.7586	Intermediate Similarity	NPC7563
0.7586	Intermediate Similarity	NPC320630
0.7582	Intermediate Similarity	NPC114979
0.7582	Intermediate Similarity	NPC476804
0.7582	Intermediate Similarity	NPC191476
0.7579	Intermediate Similarity	NPC111114
0.7579	Intermediate Similarity	NPC300312
0.7579	Intermediate Similarity	NPC261607
0.7556	Intermediate Similarity	NPC85772
0.7553	Intermediate Similarity	NPC115179
0.7553	Intermediate Similarity	NPC106040
0.7553	Intermediate Similarity	NPC142159
0.7553	Intermediate Similarity	NPC95364
0.7551	Intermediate Similarity	NPC208094
0.7527	Intermediate Similarity	NPC113370
0.7527	Intermediate Similarity	NPC103743
0.7527	Intermediate Similarity	NPC237540
0.7527	Intermediate Similarity	NPC476079
0.7527	Intermediate Similarity	NPC160138
0.7527	Intermediate Similarity	NPC472007
0.7526	Intermediate Similarity	NPC295347
0.7526	Intermediate Similarity	NPC304886
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC469657
0.75	Intermediate Similarity	NPC474369
0.75	Intermediate Similarity	NPC470755
0.75	Intermediate Similarity	NPC228451
0.75	Intermediate Similarity	NPC471223
0.75	Intermediate Similarity	NPC244456
0.75	Intermediate Similarity	NPC475838
0.75	Intermediate Similarity	NPC78089
0.75	Intermediate Similarity	NPC307112
0.75	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC192006
0.75	Intermediate Similarity	NPC125290
0.75	Intermediate Similarity	NPC67081
0.75	Intermediate Similarity	NPC476049
0.75	Intermediate Similarity	NPC125674
0.7476	Intermediate Similarity	NPC469853
0.7474	Intermediate Similarity	NPC77337
0.7474	Intermediate Similarity	NPC475855
0.7473	Intermediate Similarity	NPC131669
0.7473	Intermediate Similarity	NPC473390
0.7473	Intermediate Similarity	NPC250315
0.7471	Intermediate Similarity	NPC473223
0.747	Intermediate Similarity	NPC313444
0.7451	Intermediate Similarity	NPC309190
0.7451	Intermediate Similarity	NPC472868
0.7449	Intermediate Similarity	NPC172998
0.7449	Intermediate Similarity	NPC299396
0.7449	Intermediate Similarity	NPC301596
0.7447	Intermediate Similarity	NPC476805
0.7447	Intermediate Similarity	NPC475819
0.7444	Intermediate Similarity	NPC42470
0.7444	Intermediate Similarity	NPC24417
0.7444	Intermediate Similarity	NPC52861
0.7444	Intermediate Similarity	NPC25684
0.7444	Intermediate Similarity	NPC471325
0.7444	Intermediate Similarity	NPC301477
0.7444	Intermediate Similarity	NPC141810
0.7444	Intermediate Similarity	NPC281949
0.7444	Intermediate Similarity	NPC112868
0.7442	Intermediate Similarity	NPC476355
0.7442	Intermediate Similarity	NPC227396
0.7426	Intermediate Similarity	NPC471599
0.7423	Intermediate Similarity	NPC167219
0.7423	Intermediate Similarity	NPC474247
0.7423	Intermediate Similarity	NPC477241
0.7423	Intermediate Similarity	NPC474338
0.7419	Intermediate Similarity	NPC203795
0.7419	Intermediate Similarity	NPC469483
0.7419	Intermediate Similarity	NPC261721
0.7419	Intermediate Similarity	NPC198314
0.7419	Intermediate Similarity	NPC107787
0.7419	Intermediate Similarity	NPC150755
0.7419	Intermediate Similarity	NPC472009
0.7419	Intermediate Similarity	NPC164393
0.7416	Intermediate Similarity	NPC178277
0.7416	Intermediate Similarity	NPC63649
0.7416	Intermediate Similarity	NPC270126
0.7416	Intermediate Similarity	NPC472965
0.7416	Intermediate Similarity	NPC264227
0.7396	Intermediate Similarity	NPC45579
0.7396	Intermediate Similarity	NPC193396
0.7396	Intermediate Similarity	NPC133698
0.7396	Intermediate Similarity	NPC472705
0.7396	Intermediate Similarity	NPC32944
0.7391	Intermediate Similarity	NPC243618
0.7391	Intermediate Similarity	NPC115786
0.7391	Intermediate Similarity	NPC295799
0.7391	Intermediate Similarity	NPC82297
0.7391	Intermediate Similarity	NPC158756
0.7391	Intermediate Similarity	NPC470918
0.7391	Intermediate Similarity	NPC31086
0.7391	Intermediate Similarity	NPC70424
0.7386	Intermediate Similarity	NPC86917
0.7386	Intermediate Similarity	NPC472014
0.7386	Intermediate Similarity	NPC57744
0.7386	Intermediate Similarity	NPC187568
0.7386	Intermediate Similarity	NPC471225
0.7386	Intermediate Similarity	NPC41780
0.7381	Intermediate Similarity	NPC232812
0.7381	Intermediate Similarity	NPC67608
0.7379	Intermediate Similarity	NPC469852
0.7374	Intermediate Similarity	NPC239895
0.7374	Intermediate Similarity	NPC69385
0.7374	Intermediate Similarity	NPC20066
0.7368	Intermediate Similarity	NPC218927
0.7368	Intermediate Similarity	NPC295312
0.7368	Intermediate Similarity	NPC36668
0.7368	Intermediate Similarity	NPC118011
0.7368	Intermediate Similarity	NPC206001
0.7363	Intermediate Similarity	NPC229825
0.7363	Intermediate Similarity	NPC89555
0.7363	Intermediate Similarity	NPC474252
0.7363	Intermediate Similarity	NPC173609
0.7356	Intermediate Similarity	NPC244166
0.7353	Intermediate Similarity	NPC25666
0.7353	Intermediate Similarity	NPC271059
0.7347	Intermediate Similarity	NPC272050
0.7347	Intermediate Similarity	NPC209355
0.7347	Intermediate Similarity	NPC67584
0.7347	Intermediate Similarity	NPC234339
0.7347	Intermediate Similarity	NPC273197
0.7347	Intermediate Similarity	NPC20546
0.734	Intermediate Similarity	NPC312561
0.734	Intermediate Similarity	NPC142583
0.7333	Intermediate Similarity	NPC160582
0.7333	Intermediate Similarity	NPC47951
0.7327	Intermediate Similarity	NPC206079
0.7327	Intermediate Similarity	NPC219038
0.7326	Intermediate Similarity	NPC238948
0.7326	Intermediate Similarity	NPC12815
0.7326	Intermediate Similarity	NPC215745
0.732	Intermediate Similarity	NPC469692
0.732	Intermediate Similarity	NPC59646
0.732	Intermediate Similarity	NPC273579
0.732	Intermediate Similarity	NPC472871
0.732	Intermediate Similarity	NPC475912
0.732	Intermediate Similarity	NPC288240
0.732	Intermediate Similarity	NPC162205
0.732	Intermediate Similarity	NPC135776
0.732	Intermediate Similarity	NPC295204

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 NPC473658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1382
0.2-0.3	3458
0.3-0.4	2687
0.4-0.5	1046
0.5-0.6	342
0.6-0.7	77
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7667	Intermediate Similarity	NPD7154	Phase 3
0.7586	Intermediate Similarity	NPD4756	Discovery
0.7474	Intermediate Similarity	NPD5785	Approved
0.7473	Intermediate Similarity	NPD5362	Discontinued
0.7312	Intermediate Similarity	NPD5363	Approved
0.7174	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4269	Approved
0.7113	Intermediate Similarity	NPD6698	Approved
0.7113	Intermediate Similarity	NPD46	Approved
0.7103	Intermediate Similarity	NPD6371	Approved
0.7065	Intermediate Similarity	NPD5369	Approved
0.7053	Intermediate Similarity	NPD5786	Approved
0.7041	Intermediate Similarity	NPD5281	Approved
0.7041	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4252	Approved
0.6957	Remote Similarity	NPD4821	Approved
0.6957	Remote Similarity	NPD4820	Approved
0.6957	Remote Similarity	NPD4822	Approved
0.6957	Remote Similarity	NPD4819	Approved
0.6947	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5282	Discontinued
0.6837	Remote Similarity	NPD1695	Approved
0.6822	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5209	Approved
0.6778	Remote Similarity	NPD8039	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4268	Approved
0.6739	Remote Similarity	NPD4271	Approved
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD4790	Discontinued
0.6701	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6635	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.6628	Remote Similarity	NPD7331	Phase 2
0.66	Remote Similarity	NPD7838	Discovery
0.6598	Remote Similarity	NPD1694	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD5693	Phase 1
0.6512	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4225	Approved
0.6458	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7839	Suspended
0.6437	Remote Similarity	NPD3704	Approved
0.6436	Remote Similarity	NPD5207	Approved
0.6436	Remote Similarity	NPD5692	Phase 3
0.6429	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.64	Remote Similarity	NPD4518	Approved
0.6373	Remote Similarity	NPD7637	Suspended
0.6373	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6050	Approved
0.6373	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD5280	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD4623	Approved
0.6364	Remote Similarity	NPD4694	Approved
0.6364	Remote Similarity	NPD4519	Discontinued
0.6339	Remote Similarity	NPD2067	Discontinued
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5370	Suspended
0.6337	Remote Similarity	NPD4753	Phase 2
0.6337	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5909	Discontinued
0.6322	Remote Similarity	NPD7341	Phase 2
0.6321	Remote Similarity	NPD7638	Approved
0.6289	Remote Similarity	NPD4223	Phase 3
0.6289	Remote Similarity	NPD4221	Approved
0.6279	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6647	Phase 2
0.6238	Remote Similarity	NPD5737	Approved
0.6238	Remote Similarity	NPD6672	Approved
0.6226	Remote Similarity	NPD7902	Approved
0.6224	Remote Similarity	NPD6110	Phase 1
0.6218	Remote Similarity	NPD8513	Phase 3
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5701	Approved
0.6214	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD6684	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD5330	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5210	Approved
0.619	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD6080	Approved
0.6176	Remote Similarity	NPD6904	Approved
0.6176	Remote Similarity	NPD6673	Approved
0.6162	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD4197	Approved
0.6162	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6686	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD4202	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6008	Approved
0.6117	Remote Similarity	NPD4096	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.61	Remote Similarity	NPD5329	Approved
0.6095	Remote Similarity	NPD7748	Approved
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.6082	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5208	Approved
0.6078	Remote Similarity	NPD6903	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4755	Approved
0.6067	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7515	Phase 2
0.6055	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5205	Approved
0.604	Remote Similarity	NPD5690	Phase 2
0.604	Remote Similarity	NPD4690	Approved
0.604	Remote Similarity	NPD3618	Phase 1
0.604	Remote Similarity	NPD4689	Approved
0.604	Remote Similarity	NPD4693	Phase 3
0.604	Remote Similarity	NPD4688	Approved
0.604	Remote Similarity	NPD4138	Approved
0.6038	Remote Similarity	NPD5654	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6017	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD4786	Approved
0.5977	Remote Similarity	NPD4194	Approved
0.5977	Remote Similarity	NPD4193	Approved
0.5977	Remote Similarity	NPD4192	Approved
0.5977	Remote Similarity	NPD4191	Approved
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD6404	Discontinued
0.5963	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD3667	Approved
0.595	Remote Similarity	NPD7503	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD6001	Approved
0.5943	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5959	Approved
0.5918	Remote Similarity	NPD7332	Phase 2
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5223	Approved
0.5906	Remote Similarity	NPD7260	Phase 2
0.59	Remote Similarity	NPD4788	Approved
0.59	Remote Similarity	NPD6695	Phase 3
0.5897	Remote Similarity	NPD4632	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