NPASS Compound

Structure

CID327623 OpenBabel06191716192D 30 35 0 0 1 0 0 0 0 0999 V2000 -4.7369 -4.5943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6682 -5.4987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1490 -1.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5507 -1.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4017 -1.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6436 -1.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2010 -0.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3622 -0.8856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3908 -1.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6996 -2.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7183 -1.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4193 -4.1210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6405 -2.7439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9414 -4.7380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2979 -1.9452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7908 -0.5841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8870 -1.2426 0.0000 C 0 0 1 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 -2.0094 -2.0537 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7925 -1.8804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4469 -2.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6971 0.0448 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6153 0.6878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1821 -2.8433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1017 -3.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6238 -4.2647 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3062 -3.7913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5302 -2.0041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1164 -2.2103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 9 21 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 13 30 1 0 0 0 0 16 5 1 6 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 7 1 1 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 8 1 1 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 11 1 1 0 0 0 19 24 1 0 0 0 0 20 11 1 6 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 25 26 1 0 0 0 0 26 27 2 3 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.25
Volume:	431.098
LogP:	5.445
LogD:	5.005
LogS:	-4.616
# Rotatable Bonds:	8
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	5.507
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.739
MDCK Permeability:	0.00013152231986168772
Pgp-inhibitor:	0.982
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	97.17096710205078%
Volume Distribution (VD):	0.945
Pgp-substrate:	1.2945468425750732%

ADMET: Metabolism

CYP1A2-inhibitor:	0.712
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.878
CYP2D6-substrate:	0.628
CYP3A4-inhibitor:	0.975
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	16.487
Half-life (T1/2):	0.37

ADMET: Toxicity

hERG Blockers:	0.189
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.69
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.312
Skin Sensitization:	0.08
Carcinogencity:	0.317
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC327623

Natural Product ID:	NPC327623
*Common Name:**	MZNYKIXDEPFZJF-VOMQUASUSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Endiandramide B
Standard InCHIKey:	MZNYKIXDEPFZJF-VOMQUASUSA-N
Standard InCHI:	InChI=1S/C26H33NO3/c1-14(2)12-27-26(28)25-18-8-7-17-20(25)11-19-16(23(18)24(17)19)5-3-4-15-6-9-21-22(10-15)30-13-29-21/h6-10,14,16-20,23-25H,3-5,11-13H2,1-2H3,(H,27,28)/t16-,17+,18-,19-,20-,23-,24-,25-/m0/s1
SMILES:	CC(C)CNC(=O)C1C2CC3C(C4C1C=CC2C34)CCCC5=CC6=C(C=C5)OCO6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821990
PubChem CID:	56658431
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	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
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Emax	=	72.07	%	PMID[482890]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	16400.0	nM	PMID[482890]

☑ 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 NPC327623 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	255
0.1-0.2	1372
0.2-0.3	3664
0.3-0.4	11749
0.4-0.5	8833
0.5-0.6	12590
0.6-0.7	3948
0.7-0.8	272
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC275150
0.8824	High Similarity	NPC191302
0.8623	High Similarity	NPC147247
0.8623	High Similarity	NPC246974
0.8551	High Similarity	NPC99798
0.8551	High Similarity	NPC157740
0.8551	High Similarity	NPC41331
0.8551	High Similarity	NPC291449
0.8478	Intermediate Similarity	NPC156944
0.8425	Intermediate Similarity	NPC323601
0.8414	Intermediate Similarity	NPC318575
0.8406	Intermediate Similarity	NPC170583
0.8406	Intermediate Similarity	NPC152186
0.8406	Intermediate Similarity	NPC71105
0.8406	Intermediate Similarity	NPC246133
0.8406	Intermediate Similarity	NPC182147
0.8406	Intermediate Similarity	NPC207541
0.8345	Intermediate Similarity	NPC251466
0.8333	Intermediate Similarity	NPC300955
0.8219	Intermediate Similarity	NPC231719
0.8219	Intermediate Similarity	NPC52968
0.8146	Intermediate Similarity	NPC189054
0.8099	Intermediate Similarity	NPC469977
0.8042	Intermediate Similarity	NPC470706
0.8028	Intermediate Similarity	NPC177167
0.8014	Intermediate Similarity	NPC17348
0.8	Intermediate Similarity	NPC249788
0.8	Intermediate Similarity	NPC227002
0.7905	Intermediate Similarity	NPC254610
0.7857	Intermediate Similarity	NPC80241
0.7857	Intermediate Similarity	NPC301641
0.7842	Intermediate Similarity	NPC344161
0.7832	Intermediate Similarity	NPC40352
0.7832	Intermediate Similarity	NPC213711
0.7832	Intermediate Similarity	NPC274356
0.7823	Intermediate Similarity	NPC284855
0.7823	Intermediate Similarity	NPC282477
0.7823	Intermediate Similarity	NPC473463
0.7801	Intermediate Similarity	NPC30462
0.78	Intermediate Similarity	NPC77572
0.7778	Intermediate Similarity	NPC100129
0.774	Intermediate Similarity	NPC114102
0.7708	Intermediate Similarity	NPC301713
0.7703	Intermediate Similarity	NPC218530
0.7692	Intermediate Similarity	NPC77359
0.7687	Intermediate Similarity	NPC476345
0.7677	Intermediate Similarity	NPC16436
0.7662	Intermediate Similarity	NPC145304
0.7655	Intermediate Similarity	NPC153990
0.7639	Intermediate Similarity	NPC9067
0.7635	Intermediate Similarity	NPC219671
0.7635	Intermediate Similarity	NPC147616
0.7635	Intermediate Similarity	NPC313737
0.7635	Intermediate Similarity	NPC104077
0.7635	Intermediate Similarity	NPC6854
0.7635	Intermediate Similarity	NPC285078
0.7635	Intermediate Similarity	NPC259742
0.7619	Intermediate Similarity	NPC134764
0.7619	Intermediate Similarity	NPC275950
0.7619	Intermediate Similarity	NPC171550
0.7603	Intermediate Similarity	NPC155838
0.76	Intermediate Similarity	NPC174191
0.7595	Intermediate Similarity	NPC474560
0.7584	Intermediate Similarity	NPC169973
0.7568	Intermediate Similarity	NPC214869
0.7568	Intermediate Similarity	NPC130595
0.7568	Intermediate Similarity	NPC93882
0.7551	Intermediate Similarity	NPC195749
0.7551	Intermediate Similarity	NPC35961
0.7551	Intermediate Similarity	NPC52029
0.7548	Intermediate Similarity	NPC5462
0.7534	Intermediate Similarity	NPC64948
0.7534	Intermediate Similarity	NPC158737
0.7534	Intermediate Similarity	NPC186898
0.7517	Intermediate Similarity	NPC228771
0.7517	Intermediate Similarity	NPC471505
0.7517	Intermediate Similarity	NPC106739
0.7517	Intermediate Similarity	NPC97316
0.7517	Intermediate Similarity	NPC29008
0.7517	Intermediate Similarity	NPC266705
0.7516	Intermediate Similarity	NPC476336
0.75	Intermediate Similarity	NPC255550
0.75	Intermediate Similarity	NPC181079
0.75	Intermediate Similarity	NPC31279
0.75	Intermediate Similarity	NPC173308
0.75	Intermediate Similarity	NPC308885
0.7484	Intermediate Similarity	NPC52475
0.7483	Intermediate Similarity	NPC142547
0.7483	Intermediate Similarity	NPC160380
0.7483	Intermediate Similarity	NPC226862
0.7483	Intermediate Similarity	NPC38996
0.7483	Intermediate Similarity	NPC165128
0.7483	Intermediate Similarity	NPC158471
0.7483	Intermediate Similarity	NPC135777
0.7483	Intermediate Similarity	NPC57119
0.7482	Intermediate Similarity	NPC473264
0.7482	Intermediate Similarity	NPC475815
0.7482	Intermediate Similarity	NPC47194
0.7468	Intermediate Similarity	NPC211296
0.7467	Intermediate Similarity	NPC196937
0.7452	Intermediate Similarity	NPC33832
0.7451	Intermediate Similarity	NPC156376
0.7451	Intermediate Similarity	NPC178290
0.745	Intermediate Similarity	NPC477706
0.7447	Intermediate Similarity	NPC474040
0.7438	Intermediate Similarity	NPC18614
0.7436	Intermediate Similarity	NPC473575
0.7432	Intermediate Similarity	NPC476748
0.7426	Intermediate Similarity	NPC127326
0.7419	Intermediate Similarity	NPC191231
0.7419	Intermediate Similarity	NPC302506
0.7419	Intermediate Similarity	NPC246947
0.7417	Intermediate Similarity	NPC47181
0.7415	Intermediate Similarity	NPC251571
0.74	Intermediate Similarity	NPC321502
0.7396	Intermediate Similarity	NPC474051
0.7394	Intermediate Similarity	NPC281298
0.7394	Intermediate Similarity	NPC310338
0.7389	Intermediate Similarity	NPC271607
0.7389	Intermediate Similarity	NPC280717
0.7386	Intermediate Similarity	NPC196420
0.7386	Intermediate Similarity	NPC185908
0.7383	Intermediate Similarity	NPC233224
0.7383	Intermediate Similarity	NPC477705
0.7383	Intermediate Similarity	NPC477694
0.7383	Intermediate Similarity	NPC271208
0.7383	Intermediate Similarity	NPC63574
0.7381	Intermediate Similarity	NPC476751
0.7379	Intermediate Similarity	NPC31344
0.7379	Intermediate Similarity	NPC317769
0.7372	Intermediate Similarity	NPC477898
0.7368	Intermediate Similarity	NPC150534
0.7368	Intermediate Similarity	NPC184938
0.7368	Intermediate Similarity	NPC18576
0.7368	Intermediate Similarity	NPC101624
0.7365	Intermediate Similarity	NPC307050
0.7365	Intermediate Similarity	NPC277458
0.7355	Intermediate Similarity	NPC472711
0.7355	Intermediate Similarity	NPC471908
0.7346	Intermediate Similarity	NPC76079
0.7343	Intermediate Similarity	NPC56214
0.7343	Intermediate Similarity	NPC242885
0.7343	Intermediate Similarity	NPC95614
0.7343	Intermediate Similarity	NPC53596
0.7343	Intermediate Similarity	NPC232316
0.7343	Intermediate Similarity	NPC471308
0.7343	Intermediate Similarity	NPC289330
0.7343	Intermediate Similarity	NPC165133
0.7343	Intermediate Similarity	NPC160120
0.7343	Intermediate Similarity	NPC117780
0.7343	Intermediate Similarity	NPC17388
0.7343	Intermediate Similarity	NPC227217
0.7338	Intermediate Similarity	NPC193666
0.7338	Intermediate Similarity	NPC165106
0.7338	Intermediate Similarity	NPC88640
0.7338	Intermediate Similarity	NPC123526
0.7333	Intermediate Similarity	NPC227160
0.7333	Intermediate Similarity	NPC82111
0.7333	Intermediate Similarity	NPC192255
0.7329	Intermediate Similarity	NPC148898
0.7329	Intermediate Similarity	NPC275027
0.7325	Intermediate Similarity	NPC253015
0.7325	Intermediate Similarity	NPC217635
0.7325	Intermediate Similarity	NPC471667
0.7325	Intermediate Similarity	NPC179521
0.7325	Intermediate Similarity	NPC471065
0.7325	Intermediate Similarity	NPC84181
0.7325	Intermediate Similarity	NPC79429
0.732	Intermediate Similarity	NPC95366
0.732	Intermediate Similarity	NPC193528
0.732	Intermediate Similarity	NPC248505
0.732	Intermediate Similarity	NPC41473
0.732	Intermediate Similarity	NPC204848
0.732	Intermediate Similarity	NPC312770
0.732	Intermediate Similarity	NPC160607
0.732	Intermediate Similarity	NPC14600
0.7319	Intermediate Similarity	NPC166837
0.7317	Intermediate Similarity	NPC69360
0.731	Intermediate Similarity	NPC471314
0.731	Intermediate Similarity	NPC471315
0.7305	Intermediate Similarity	NPC33900
0.7305	Intermediate Similarity	NPC9341
0.7305	Intermediate Similarity	NPC81067
0.7303	Intermediate Similarity	NPC471942
0.7303	Intermediate Similarity	NPC90083
0.7303	Intermediate Similarity	NPC170779
0.7296	Intermediate Similarity	NPC475959
0.7289	Intermediate Similarity	NPC320104
0.7289	Intermediate Similarity	NPC218614
0.7285	Intermediate Similarity	NPC7744
0.7278	Intermediate Similarity	NPC43508
0.7278	Intermediate Similarity	NPC272619
0.7278	Intermediate Similarity	NPC235195
0.7278	Intermediate Similarity	NPC279298
0.7278	Intermediate Similarity	NPC476301
0.7278	Intermediate Similarity	NPC474953
0.7278	Intermediate Similarity	NPC19862
0.7278	Intermediate Similarity	NPC38041
0.7278	Intermediate Similarity	NPC22150
0.7278	Intermediate Similarity	NPC286245

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 NPC327623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	710
0.2-0.3	1094
0.3-0.4	2761
0.4-0.5	2604
0.5-0.6	1402
0.6-0.7	363
0.7-0.8	34
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
0.8014	Intermediate Similarity	NPD2157	Approved
0.8	Intermediate Similarity	NPD6331	Phase 2
0.7973	Intermediate Similarity	NPD2161	Phase 2
0.7785	Intermediate Similarity	NPD4108	Discontinued
0.7771	Intermediate Similarity	NPD7028	Phase 2
0.7712	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2674	Phase 3
0.7516	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1669	Approved
0.75	Intermediate Similarity	NPD3145	Approved
0.75	Intermediate Similarity	NPD3144	Approved
0.7419	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1712	Approved
0.74	Intermediate Similarity	NPD3620	Phase 2
0.74	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1357	Approved
0.7383	Intermediate Similarity	NPD5109	Approved
0.7383	Intermediate Similarity	NPD5110	Phase 2
0.7383	Intermediate Similarity	NPD5111	Phase 2
0.7361	Intermediate Similarity	NPD3705	Approved
0.7342	Intermediate Similarity	NPD4739	Approved
0.7338	Intermediate Similarity	NPD1375	Discontinued
0.7338	Intermediate Similarity	NPD5283	Phase 1
0.7296	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD52	Approved
0.7296	Intermediate Similarity	NPD7526	Approved
0.729	Intermediate Similarity	NPD7153	Discontinued
0.7273	Intermediate Similarity	NPD7833	Phase 2
0.7273	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7831	Phase 2
0.7239	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4624	Approved
0.7219	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2922	Phase 1
0.72	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4097	Suspended
0.7169	Intermediate Similarity	NPD5604	Discontinued
0.7169	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7124	Intermediate Similarity	NPD5735	Approved
0.7124	Intermediate Similarity	NPD3657	Discovery
0.7119	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD709	Approved
0.7107	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2667	Approved
0.7103	Intermediate Similarity	NPD2668	Approved
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6353	Approved
0.7078	Intermediate Similarity	NPD2492	Phase 1
0.7075	Intermediate Similarity	NPD2230	Approved
0.7075	Intermediate Similarity	NPD2233	Approved
0.7075	Intermediate Similarity	NPD2232	Approved
0.7071	Intermediate Similarity	NPD228	Approved
0.7059	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4005	Discontinued
0.7039	Intermediate Similarity	NPD5718	Phase 2
0.7032	Intermediate Similarity	NPD6896	Approved
0.7032	Intermediate Similarity	NPD6895	Approved
0.7027	Intermediate Similarity	NPD5327	Phase 3
0.7025	Intermediate Similarity	NPD6674	Discontinued
0.702	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD776	Approved
0.6988	Remote Similarity	NPD5772	Approved
0.6988	Remote Similarity	NPD5773	Approved
0.6987	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7037	Approved
0.6957	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4140	Approved
0.6941	Remote Similarity	NPD7199	Phase 2
0.6937	Remote Similarity	NPD5241	Discontinued
0.6933	Remote Similarity	NPD5699	Approved
0.6928	Remote Similarity	NPD1039	Discontinued
0.6928	Remote Similarity	NPD5722	Discontinued
0.6928	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD4237	Approved
0.6918	Remote Similarity	NPD4236	Phase 3
0.6905	Remote Similarity	NPD4965	Approved
0.6905	Remote Similarity	NPD4967	Phase 2
0.6905	Remote Similarity	NPD4966	Approved
0.6901	Remote Similarity	NPD821	Approved
0.6901	Remote Similarity	NPD7315	Approved
0.6887	Remote Similarity	NPD6584	Phase 3
0.6886	Remote Similarity	NPD2977	Approved
0.6886	Remote Similarity	NPD2978	Approved
0.686	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2969	Approved
0.686	Remote Similarity	NPD2970	Approved
0.6855	Remote Similarity	NPD2808	Discontinued
0.6855	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2122	Discontinued
0.6824	Remote Similarity	NPD6234	Discontinued
0.6821	Remote Similarity	NPD2898	Approved
0.6821	Remote Similarity	NPD27	Approved
0.6821	Remote Similarity	NPD2489	Approved
0.6818	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7119	Phase 2
0.6815	Remote Similarity	NPD6111	Discontinued
0.6813	Remote Similarity	NPD5177	Phase 3
0.681	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4123	Phase 3
0.6802	Remote Similarity	NPD3051	Approved
0.6792	Remote Similarity	NPD5763	Approved
0.6792	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD4210	Discontinued
0.6786	Remote Similarity	NPD5929	Approved
0.6776	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7477	Discontinued
0.6768	Remote Similarity	NPD4319	Phase 2
0.6766	Remote Similarity	NPD4772	Phase 2
0.6766	Remote Similarity	NPD4773	Phase 2
0.6757	Remote Similarity	NPD4626	Approved
0.6753	Remote Similarity	NPD1024	Discontinued
0.6746	Remote Similarity	NPD2560	Approved
0.6746	Remote Similarity	NPD2563	Approved
0.6746	Remote Similarity	NPD5977	Approved
0.6746	Remote Similarity	NPD5978	Approved
0.6744	Remote Similarity	NPD8127	Discontinued
0.6731	Remote Similarity	NPD3109	Approved
0.6731	Remote Similarity	NPD1558	Phase 1
0.6731	Remote Similarity	NPD3110	Approved
0.6731	Remote Similarity	NPD2238	Phase 2
0.6728	Remote Similarity	NPD2219	Phase 1
0.6727	Remote Similarity	NPD4727	Phase 1
0.6708	Remote Similarity	NPD3060	Approved
0.6707	Remote Similarity	NPD7019	Approved
0.6707	Remote Similarity	NPD7020	Approved
0.6705	Remote Similarity	NPD6071	Discontinued
0.6704	Remote Similarity	NPD7281	Phase 3
0.6704	Remote Similarity	NPD7280	Phase 3
0.6689	Remote Similarity	NPD6583	Phase 3
0.6689	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6582	Phase 2
0.6687	Remote Similarity	NPD7124	Phase 2
0.6686	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5090	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD5089	Approved
0.6667	Remote Similarity	NPD4055	Discovery
0.6667	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7228	Approved
0.6646	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2653	Approved
0.6646	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4357	Discontinued
0.6645	Remote Similarity	NPD3027	Phase 3
0.6645	Remote Similarity	NPD1283	Approved
0.6644	Remote Similarity	NPD7157	Approved
0.6644	Remote Similarity	NPD6387	Discontinued
0.6629	Remote Similarity	NPD4481	Phase 3
0.6627	Remote Similarity	NPD5714	Approved
0.6624	Remote Similarity	NPD4060	Phase 1
0.6623	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2861	Phase 2
0.6622	Remote Similarity	NPD3091	Approved
0.662	Remote Similarity	NPD2684	Approved
0.6612	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7312	Approved
0.6611	Remote Similarity	NPD7313	Approved
0.6611	Remote Similarity	NPD7311	Approved
0.6611	Remote Similarity	NPD7310	Approved
0.6607	Remote Similarity	NPD4675	Approved
0.6607	Remote Similarity	NPD4678	Approved
0.6607	Remote Similarity	NPD6875	Approved
0.6607	Remote Similarity	NPD1642	Discontinued
0.6607	Remote Similarity	NPD6876	Approved
0.6606	Remote Similarity	NPD4584	Approved
0.6606	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4162	Approved
0.6579	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5691	Approved
0.6577	Remote Similarity	NPD4093	Discontinued
0.6575	Remote Similarity	NPD7309	Approved
0.6573	Remote Similarity	NPD3021	Approved
0.6573	Remote Similarity	NPD3022	Approved
0.6568	Remote Similarity	NPD6873	Phase 2
0.6562	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1423	Approved
0.6561	Remote Similarity	NPD7265	Discontinued
0.6557	Remote Similarity	NPD6841	Approved
0.6557	Remote Similarity	NPD6843	Phase 3
0.6557	Remote Similarity	NPD6842	Approved
0.6556	Remote Similarity	NPD3092	Approved
0.6554	Remote Similarity	NPD5536	Phase 2
0.6552	Remote Similarity	NPD7843	Approved
0.6541	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7095	Approved
0.6536	Remote Similarity	NPD8651	Approved
0.6536	Remote Similarity	NPD7258	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