NPASS Compound

Structure

NPC20066 OpenBabel07101719522D 27 28 0 0 1 0 0 0 0 0999 V2000 -4.0226 -1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7991 -4.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8672 -3.6225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0908 -0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 -2.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3496 -1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1260 -4.5884 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -0.4659 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 -3.3155 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0920 -4.8473 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3508 -5.8132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3167 -6.0720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6437 -6.5203 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 1 0 0 0 0 2 14 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 6 0 0 0 17 27 1 0 0 0 0 18 21 1 1 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	394.218
LogP:	2.241
LogD:	1.422
LogS:	-4.163
# Rotatable Bonds:	7
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	4.818
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.244
MDCK Permeability:	3.936384746339172e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	92.42911529541016%
Volume Distribution (VD):	0.266
Pgp-substrate:	3.246015787124634%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	8.234
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.076
Skin Sensitization:	0.682
Carcinogencity:	0.05
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.656

Download Data

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

Natural Product: NPC20066

Natural Product ID:	NPC20066
*Common Name:**	Bicycloalternarene E
IUPAC Name:	(2E,6E)-9-[(2S,3S,6R)-3,6-dihydroxy-2-methyl-5-oxo-4,6,7,8-tetrahydro-3H-chromen-2-yl]-2,6-dimethylnona-2,6-dienoic acid
Synonyms:
Standard InCHIKey:	IBSUBHFSOZBARY-NQKOLOIPSA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-13(6-4-8-14(2)20(25)26)7-5-11-21(3)18(23)12-15-17(27-21)10-9-16(22)19(15)24/h7-8,16,18,22-23H,4-6,9-12H2,1-3H3,(H,25,26)/b13-7+,14-8+/t16-,18+,21+/m1/s1
SMILES:	C/C(=CCC[C@]1(C)OC2=C(C[C@@H]1O)C(=O)[C@@H](CC2)O)/CC/C=C(/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431883
PubChem CID:	72704865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans

*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
NPO32811	Alternaria sp. JJY-32	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128115]

☑ 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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[497500]

☑ 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 NPC20066 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	216
0.1-0.2	1215
0.2-0.3	4432
0.3-0.4	8033
0.4-0.5	15668
0.5-0.6	8283
0.6-0.7	4031
0.7-0.8	785
0.8-0.85	26
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC300584
0.9121	High Similarity	NPC265856
0.871	High Similarity	NPC166554
0.8617	High Similarity	NPC146852
0.8526	High Similarity	NPC61275
0.8495	Intermediate Similarity	NPC472008
0.8387	Intermediate Similarity	NPC179659
0.8387	Intermediate Similarity	NPC472007
0.8316	Intermediate Similarity	NPC471399
0.828	Intermediate Similarity	NPC472009
0.8269	Intermediate Similarity	NPC471400
0.8218	Intermediate Similarity	NPC39996
0.8163	Intermediate Similarity	NPC91408
0.8125	Intermediate Similarity	NPC469464
0.81	Intermediate Similarity	NPC306908
0.7981	Intermediate Similarity	NPC469852
0.7979	Intermediate Similarity	NPC77971
0.7959	Intermediate Similarity	NPC475912
0.7959	Intermediate Similarity	NPC295204
0.7959	Intermediate Similarity	NPC273579
0.7959	Intermediate Similarity	NPC288240
0.7959	Intermediate Similarity	NPC162205
0.7941	Intermediate Similarity	NPC471401
0.7921	Intermediate Similarity	NPC35717
0.7905	Intermediate Similarity	NPC469853
0.7879	Intermediate Similarity	NPC474035
0.7879	Intermediate Similarity	NPC81386
0.7879	Intermediate Similarity	NPC71589
0.7872	Intermediate Similarity	NPC70424
0.7872	Intermediate Similarity	NPC243618
0.7872	Intermediate Similarity	NPC474251
0.787	Intermediate Similarity	NPC66108
0.7857	Intermediate Similarity	NPC30515
0.785	Intermediate Similarity	NPC5103
0.7826	Intermediate Similarity	NPC470947
0.7826	Intermediate Similarity	NPC470945
0.7826	Intermediate Similarity	NPC470946
0.7812	Intermediate Similarity	NPC471738
0.78	Intermediate Similarity	NPC14961
0.78	Intermediate Similarity	NPC36954
0.78	Intermediate Similarity	NPC270013
0.78	Intermediate Similarity	NPC279313
0.7789	Intermediate Similarity	NPC21469
0.7788	Intermediate Similarity	NPC472755
0.7788	Intermediate Similarity	NPC475945
0.7788	Intermediate Similarity	NPC472001
0.7788	Intermediate Similarity	NPC469980
0.7788	Intermediate Similarity	NPC118902
0.7788	Intermediate Similarity	NPC104161
0.7788	Intermediate Similarity	NPC475871
0.7778	Intermediate Similarity	NPC81419
0.7778	Intermediate Similarity	NPC179746
0.7767	Intermediate Similarity	NPC128733
0.7767	Intermediate Similarity	NPC476270
0.7767	Intermediate Similarity	NPC185141
0.7767	Intermediate Similarity	NPC110443
0.7767	Intermediate Similarity	NPC133907
0.7767	Intermediate Similarity	NPC46998
0.7757	Intermediate Similarity	NPC38154
0.7755	Intermediate Similarity	NPC476004
0.7755	Intermediate Similarity	NPC51004
0.7755	Intermediate Similarity	NPC474761
0.7745	Intermediate Similarity	NPC83895
0.7745	Intermediate Similarity	NPC187761
0.7732	Intermediate Similarity	NPC87189
0.7732	Intermediate Similarity	NPC228415
0.7732	Intermediate Similarity	NPC153805
0.7732	Intermediate Similarity	NPC202672
0.7692	Intermediate Similarity	NPC149371
0.7692	Intermediate Similarity	NPC474747
0.7679	Intermediate Similarity	NPC251310
0.7677	Intermediate Similarity	NPC473321
0.7677	Intermediate Similarity	NPC208886
0.7677	Intermediate Similarity	NPC470379
0.7677	Intermediate Similarity	NPC470373
0.7677	Intermediate Similarity	NPC12172
0.7677	Intermediate Similarity	NPC184463
0.7658	Intermediate Similarity	NPC478216
0.7653	Intermediate Similarity	NPC307411
0.7653	Intermediate Similarity	NPC474032
0.7647	Intermediate Similarity	NPC40812
0.7642	Intermediate Similarity	NPC472751
0.7642	Intermediate Similarity	NPC472749
0.7636	Intermediate Similarity	NPC469496
0.7636	Intermediate Similarity	NPC469454
0.7636	Intermediate Similarity	NPC469463
0.7619	Intermediate Similarity	NPC472747
0.7619	Intermediate Similarity	NPC472750
0.7615	Intermediate Similarity	NPC317107
0.7615	Intermediate Similarity	NPC179798
0.7615	Intermediate Similarity	NPC304180
0.7604	Intermediate Similarity	NPC137033
0.76	Intermediate Similarity	NPC212486
0.76	Intermediate Similarity	NPC327620
0.76	Intermediate Similarity	NPC469692
0.76	Intermediate Similarity	NPC469645
0.76	Intermediate Similarity	NPC476300
0.7596	Intermediate Similarity	NPC469851
0.7596	Intermediate Similarity	NPC47880
0.7596	Intermediate Similarity	NPC472753
0.7596	Intermediate Similarity	NPC97435
0.7596	Intermediate Similarity	NPC474742
0.7593	Intermediate Similarity	NPC141350
0.7579	Intermediate Similarity	NPC477784
0.7579	Intermediate Similarity	NPC477786
0.7579	Intermediate Similarity	NPC477785
0.7576	Intermediate Similarity	NPC473619
0.7573	Intermediate Similarity	NPC471144
0.7573	Intermediate Similarity	NPC255592
0.7573	Intermediate Similarity	NPC308567
0.7573	Intermediate Similarity	NPC261377
0.757	Intermediate Similarity	NPC3316
0.757	Intermediate Similarity	NPC266514
0.757	Intermediate Similarity	NPC144854
0.7551	Intermediate Similarity	NPC474471
0.7551	Intermediate Similarity	NPC227379
0.7549	Intermediate Similarity	NPC135576
0.7549	Intermediate Similarity	NPC476315
0.7549	Intermediate Similarity	NPC93271
0.7547	Intermediate Similarity	NPC258532
0.7547	Intermediate Similarity	NPC118911
0.7547	Intermediate Similarity	NPC472748
0.7547	Intermediate Similarity	NPC40170
0.7547	Intermediate Similarity	NPC100487
0.7547	Intermediate Similarity	NPC474741
0.7545	Intermediate Similarity	NPC90769
0.7545	Intermediate Similarity	NPC317687
0.7545	Intermediate Similarity	NPC472002
0.7526	Intermediate Similarity	NPC112685
0.7526	Intermediate Similarity	NPC164393
0.7525	Intermediate Similarity	NPC196227
0.7525	Intermediate Similarity	NPC121825
0.7525	Intermediate Similarity	NPC57405
0.7525	Intermediate Similarity	NPC303942
0.7524	Intermediate Similarity	NPC324017
0.7524	Intermediate Similarity	NPC197835
0.7524	Intermediate Similarity	NPC70369
0.7524	Intermediate Similarity	NPC189609
0.7524	Intermediate Similarity	NPC140591
0.7524	Intermediate Similarity	NPC320019
0.7524	Intermediate Similarity	NPC303653
0.7524	Intermediate Similarity	NPC291500
0.7524	Intermediate Similarity	NPC472754
0.7523	Intermediate Similarity	NPC478211
0.7523	Intermediate Similarity	NPC286880
0.7523	Intermediate Similarity	NPC99760
0.75	Intermediate Similarity	NPC329952
0.75	Intermediate Similarity	NPC192813
0.75	Intermediate Similarity	NPC472010
0.75	Intermediate Similarity	NPC154608
0.75	Intermediate Similarity	NPC475441
0.75	Intermediate Similarity	NPC141195
0.75	Intermediate Similarity	NPC288876
0.75	Intermediate Similarity	NPC142838
0.75	Intermediate Similarity	NPC179626
0.75	Intermediate Similarity	NPC277017
0.75	Intermediate Similarity	NPC9868
0.75	Intermediate Similarity	NPC264819
0.75	Intermediate Similarity	NPC47844
0.7478	Intermediate Similarity	NPC471999
0.7478	Intermediate Similarity	NPC472000
0.7477	Intermediate Similarity	NPC472645
0.7477	Intermediate Similarity	NPC56448
0.7476	Intermediate Similarity	NPC473574
0.7476	Intermediate Similarity	NPC20078
0.7475	Intermediate Similarity	NPC295312
0.7475	Intermediate Similarity	NPC307092
0.7456	Intermediate Similarity	NPC268958
0.7455	Intermediate Similarity	NPC132790
0.7455	Intermediate Similarity	NPC97939
0.7455	Intermediate Similarity	NPC100329
0.7455	Intermediate Similarity	NPC247031
0.7455	Intermediate Similarity	NPC188738
0.7453	Intermediate Similarity	NPC99266
0.7451	Intermediate Similarity	NPC272050
0.7451	Intermediate Similarity	NPC134067
0.7449	Intermediate Similarity	NPC248602
0.7447	Intermediate Similarity	NPC233377
0.7434	Intermediate Similarity	NPC156252
0.7434	Intermediate Similarity	NPC477116
0.7434	Intermediate Similarity	NPC27999
0.7431	Intermediate Similarity	NPC27814
0.7431	Intermediate Similarity	NPC77089
0.7431	Intermediate Similarity	NPC101018
0.7431	Intermediate Similarity	NPC20192
0.7429	Intermediate Similarity	NPC164598
0.7429	Intermediate Similarity	NPC181645
0.7429	Intermediate Similarity	NPC474339
0.7429	Intermediate Similarity	NPC15993
0.7429	Intermediate Similarity	NPC115862
0.7429	Intermediate Similarity	NPC470184
0.7429	Intermediate Similarity	NPC9878
0.7429	Intermediate Similarity	NPC201718
0.7426	Intermediate Similarity	NPC11456
0.7423	Intermediate Similarity	NPC471223
0.7423	Intermediate Similarity	NPC67081
0.7423	Intermediate Similarity	NPC242233
0.7423	Intermediate Similarity	NPC187529
0.7423	Intermediate Similarity	NPC182383
0.7423	Intermediate Similarity	NPC28887

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 NPC20066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1710
0.2-0.3	3623
0.3-0.4	2279
0.4-0.5	912
0.5-0.6	318
0.6-0.7	100
0.7-0.8	7
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
0.74	Intermediate Similarity	NPD46	Approved
0.74	Intermediate Similarity	NPD6698	Approved
0.7396	Intermediate Similarity	NPD6110	Phase 1
0.7327	Intermediate Similarity	NPD7983	Approved
0.7312	Intermediate Similarity	NPD4756	Discovery
0.7255	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4632	Approved
0.6991	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6053	Discontinued
0.6903	Remote Similarity	NPD6371	Approved
0.6869	Remote Similarity	NPD7154	Phase 3
0.6857	Remote Similarity	NPD5282	Discontinued
0.6838	Remote Similarity	NPD7115	Discovery
0.6807	Remote Similarity	NPD6319	Approved
0.6789	Remote Similarity	NPD5344	Discontinued
0.6786	Remote Similarity	NPD5697	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.6759	Remote Similarity	NPD4225	Approved
0.675	Remote Similarity	NPD8513	Phase 3
0.6733	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5363	Approved
0.6731	Remote Similarity	NPD7838	Discovery
0.6726	Remote Similarity	NPD6881	Approved
0.6726	Remote Similarity	NPD6011	Approved
0.6726	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6612	Remote Similarity	NPD8515	Approved
0.6612	Remote Similarity	NPD8516	Approved
0.6612	Remote Similarity	NPD5983	Phase 2
0.6612	Remote Similarity	NPD8517	Approved
0.6609	Remote Similarity	NPD7290	Approved
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.6593	Remote Similarity	NPD3704	Approved
0.6593	Remote Similarity	NPD7331	Phase 2
0.6579	Remote Similarity	NPD7320	Approved
0.6579	Remote Similarity	NPD6686	Approved
0.6579	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5211	Phase 2
0.6574	Remote Similarity	NPD7839	Suspended
0.6571	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD6847	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6411	Approved
0.6505	Remote Similarity	NPD4249	Approved
0.6504	Remote Similarity	NPD8328	Phase 3
0.6504	Remote Similarity	NPD7604	Phase 2
0.6496	Remote Similarity	NPD6882	Approved
0.6466	Remote Similarity	NPD4634	Approved
0.646	Remote Similarity	NPD5141	Approved
0.6452	Remote Similarity	NPD7492	Approved
0.6444	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4251	Approved
0.6442	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD4269	Approved
0.6436	Remote Similarity	NPD4270	Approved
0.6436	Remote Similarity	NPD6435	Approved
0.641	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1694	Approved
0.6408	Remote Similarity	NPD1696	Phase 3
0.6406	Remote Similarity	NPD7260	Phase 2
0.6404	Remote Similarity	NPD6008	Approved
0.64	Remote Similarity	NPD4695	Discontinued
0.64	Remote Similarity	NPD6616	Approved
0.64	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6336	Discontinued
0.6396	Remote Similarity	NPD5285	Approved
0.6396	Remote Similarity	NPD6648	Approved
0.6396	Remote Similarity	NPD4696	Approved
0.6396	Remote Similarity	NPD5286	Approved
0.6393	Remote Similarity	NPD6054	Approved
0.6373	Remote Similarity	NPD5362	Discontinued
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6083	Phase 2
0.6364	Remote Similarity	NPD7902	Approved
0.6349	Remote Similarity	NPD8074	Phase 3
0.6349	Remote Similarity	NPD7078	Approved
0.6341	Remote Similarity	NPD6015	Approved
0.6341	Remote Similarity	NPD6016	Approved
0.6339	Remote Similarity	NPD5223	Approved
0.6337	Remote Similarity	NPD5369	Approved
0.6333	Remote Similarity	NPD6274	Approved
0.633	Remote Similarity	NPD5695	Phase 3
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5696	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.6296	Remote Similarity	NPD6399	Phase 3
0.629	Remote Similarity	NPD5988	Approved
0.629	Remote Similarity	NPD8080	Discontinued
0.629	Remote Similarity	NPD6370	Approved
0.6283	Remote Similarity	NPD5225	Approved
0.6283	Remote Similarity	NPD5226	Approved
0.6283	Remote Similarity	NPD4633	Approved
0.6283	Remote Similarity	NPD5224	Approved
0.6281	Remote Similarity	NPD6317	Approved
0.6275	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4697	Phase 3
0.6273	Remote Similarity	NPD5221	Approved
0.6273	Remote Similarity	NPD5222	Approved
0.626	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD7639	Approved
0.625	Remote Similarity	NPD7640	Approved
0.624	Remote Similarity	NPD7642	Approved
0.6239	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD5368	Approved
0.6238	Remote Similarity	NPD4821	Approved
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4819	Approved
0.6238	Remote Similarity	NPD4252	Approved
0.6238	Remote Similarity	NPD4822	Approved
0.6238	Remote Similarity	NPD4820	Approved
0.6237	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6335	Approved
0.623	Remote Similarity	NPD6313	Approved
0.623	Remote Similarity	NPD6314	Approved
0.6228	Remote Similarity	NPD5175	Approved
0.6228	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD8293	Discontinued
0.6216	Remote Similarity	NPD5173	Approved
0.621	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6412	Phase 2
0.6204	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3197	Phase 1
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.617	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7638	Approved
0.6148	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7507	Approved
0.6132	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD7341	Phase 2
0.6117	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7829	Approved
0.6107	Remote Similarity	NPD6845	Suspended
0.6091	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7900	Approved
0.6087	Remote Similarity	NPD4754	Approved
0.608	Remote Similarity	NPD7503	Approved
0.608	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6672	Approved
0.6075	Remote Similarity	NPD5737	Approved
0.6068	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6868	Approved
0.6063	Remote Similarity	NPD8340	Approved
0.6063	Remote Similarity	NPD8342	Approved
0.6063	Remote Similarity	NPD8299	Approved
0.6063	Remote Similarity	NPD8341	Approved
0.6055	Remote Similarity	NPD6079	Approved
0.6055	Remote Similarity	NPD7637	Suspended
0.605	Remote Similarity	NPD2067	Discontinued
0.6045	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD4268	Approved
0.6038	Remote Similarity	NPD3618	Phase 1
0.6038	Remote Similarity	NPD6422	Discontinued
0.6038	Remote Similarity	NPD5279	Phase 3
0.6036	Remote Similarity	NPD5210	Approved
0.6036	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5328	Approved
0.6019	Remote Similarity	NPD1695	Approved
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD5128	Approved
0.6017	Remote Similarity	NPD4729	Approved
0.6017	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4767	Approved
0.5983	Remote Similarity	NPD4768	Approved
0.5966	Remote Similarity	NPD8132	Clinical (unspecified phase)

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