NPASS Compound

Structure

NPC475989 OpenBabel07101719152D 28 29 0 0 1 0 0 0 0 0999 V2000 2.1176 3.6221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7919 3.6221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0148 0.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 -3.1387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3990 1.6038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6460 4.3531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4027 1.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6530 -1.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8972 -1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6530 1.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0123 -1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8972 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2566 -1.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 3.1387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 -2.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5008 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6820 4.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 2.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2566 1.3543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0123 1.9570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8372 0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6449 2.9128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2626 5.2962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5929 2.8279 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 6 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 1 0 0 0 23 27 1 1 0 0 0 24 7 1 1 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.26
Volume:	428.526
LogP:	3.949
LogD:	3.912
LogS:	-4.831
# Rotatable Bonds:	4
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	4.909
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.546
MDCK Permeability:	2.227909499197267e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.443

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.532
Plasma Protein Binding (PPB):	97.93616485595703%
Volume Distribution (VD):	1.491
Pgp-substrate:	3.6757805347442627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.453
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.309
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	5.38
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.555
Carcinogencity:	0.113
Eye Corrosion:	0.531
Eye Irritation:	0.09
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475989

Natural Product ID:	NPC475989
*Common Name:**	(1Z,3E,7E,11S, 12R,13S,14R)-13,14-Diacetoxy-11,12-Epoxy Cembra-1,3,7-Triene
IUPAC Name:	[(1S,4E,8E,10Z,12R,13S,14R)-13-acetyl-4,8,14-trimethyl-11-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,8,10-trien-12-yl] acetate
Synonyms:
Standard InCHIKey:	CLNOLKVURQCKGV-HIRIFFSGSA-N
Standard InCHI:	InChI=1S/C24H36O4/c1-15(2)20-13-11-16(3)9-8-10-17(4)12-14-21-24(7,28-21)22(18(5)25)23(20)27-19(6)26/h10-11,13,15,21-23H,8-9,12,14H2,1-7H3/b16-11+,17-10+,20-13-/t21-,22-,23-,24-/m0/s1
SMILES:	CC1=CCCC(=CC=C(C(C(C2(C(O2)CC1)C)C(=O)C)OC(=O)C)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520567
PubChem CID:	44558960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO21438	Cladiella kashmani	Species	Alcyoniidae	Eukaryota	n.a.	African soft coral	n.a.	PMID[11087607]
NPO21438	Cladiella kashmani	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	110.0	ppm	PMID[453496]

☑ 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 NPC475989 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	228
0.1-0.2	1371
0.2-0.3	5411
0.3-0.4	12944
0.4-0.5	12775
0.5-0.6	6790
0.6-0.7	2614
0.7-0.8	549
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8765	High Similarity	NPC79277
0.8765	High Similarity	NPC475481
0.8537	High Similarity	NPC141810
0.8391	Intermediate Similarity	NPC475971
0.8375	Intermediate Similarity	NPC301525
0.8293	Intermediate Similarity	NPC617
0.8272	Intermediate Similarity	NPC474760
0.8205	Intermediate Similarity	NPC475310
0.8171	Intermediate Similarity	NPC474005
0.8148	Intermediate Similarity	NPC474447
0.8125	Intermediate Similarity	NPC474551
0.8118	Intermediate Similarity	NPC474703
0.8118	Intermediate Similarity	NPC475842
0.8118	Intermediate Similarity	NPC170377
0.8095	Intermediate Similarity	NPC42470
0.8095	Intermediate Similarity	NPC25684
0.8095	Intermediate Similarity	NPC281949
0.8095	Intermediate Similarity	NPC301477
0.8095	Intermediate Similarity	NPC471325
0.809	Intermediate Similarity	NPC51653
0.8068	Intermediate Similarity	NPC475902
0.8049	Intermediate Similarity	NPC476325
0.8049	Intermediate Similarity	NPC476264
0.8046	Intermediate Similarity	NPC474045
0.8046	Intermediate Similarity	NPC261253
0.8046	Intermediate Similarity	NPC50637
0.8025	Intermediate Similarity	NPC244166
0.8022	Intermediate Similarity	NPC476267
0.8	Intermediate Similarity	NPC238425
0.8	Intermediate Similarity	NPC475936
0.8	Intermediate Similarity	NPC20713
0.8	Intermediate Similarity	NPC472018
0.8	Intermediate Similarity	NPC474543
0.8	Intermediate Similarity	NPC35556
0.7952	Intermediate Similarity	NPC128276
0.7952	Intermediate Similarity	NPC474341
0.7931	Intermediate Similarity	NPC78089
0.7927	Intermediate Similarity	NPC271070
0.7927	Intermediate Similarity	NPC239127
0.7907	Intermediate Similarity	NPC53867
0.7907	Intermediate Similarity	NPC475947
0.7901	Intermediate Similarity	NPC330016
0.7889	Intermediate Similarity	NPC475748
0.7889	Intermediate Similarity	NPC316228
0.7882	Intermediate Similarity	NPC474894
0.7857	Intermediate Similarity	NPC178277
0.7848	Intermediate Similarity	NPC477448
0.7848	Intermediate Similarity	NPC477449
0.7841	Intermediate Similarity	NPC38576
0.7841	Intermediate Similarity	NPC469483
0.7841	Intermediate Similarity	NPC107787
0.7841	Intermediate Similarity	NPC279859
0.7831	Intermediate Similarity	NPC57744
0.7831	Intermediate Similarity	NPC97516
0.7826	Intermediate Similarity	NPC140543
0.7805	Intermediate Similarity	NPC255060
0.7802	Intermediate Similarity	NPC284185
0.7791	Intermediate Similarity	NPC89555
0.7791	Intermediate Similarity	NPC85772
0.7778	Intermediate Similarity	NPC106040
0.7778	Intermediate Similarity	NPC167145
0.7778	Intermediate Similarity	NPC115179
0.7778	Intermediate Similarity	NPC166919
0.7765	Intermediate Similarity	NPC474510
0.7765	Intermediate Similarity	NPC469920
0.7765	Intermediate Similarity	NPC474739
0.7753	Intermediate Similarity	NPC478145
0.7753	Intermediate Similarity	NPC471739
0.7753	Intermediate Similarity	NPC474765
0.7753	Intermediate Similarity	NPC266957
0.7753	Intermediate Similarity	NPC478144
0.7753	Intermediate Similarity	NPC231889
0.775	Intermediate Similarity	NPC69462
0.7738	Intermediate Similarity	NPC121200
0.7727	Intermediate Similarity	NPC261380
0.7727	Intermediate Similarity	NPC474369
0.7727	Intermediate Similarity	NPC474547
0.7701	Intermediate Similarity	NPC475622
0.7701	Intermediate Similarity	NPC108045
0.7701	Intermediate Similarity	NPC318468
0.7701	Intermediate Similarity	NPC272814
0.7692	Intermediate Similarity	NPC312042
0.7692	Intermediate Similarity	NPC62815
0.7692	Intermediate Similarity	NPC253144
0.7683	Intermediate Similarity	NPC140287
0.7683	Intermediate Similarity	NPC474758
0.7674	Intermediate Similarity	NPC476988
0.7674	Intermediate Similarity	NPC470241
0.7674	Intermediate Similarity	NPC286229
0.7667	Intermediate Similarity	NPC471047
0.7667	Intermediate Similarity	NPC469631
0.7667	Intermediate Similarity	NPC475906
0.7667	Intermediate Similarity	NPC201046
0.7667	Intermediate Similarity	NPC469653
0.7667	Intermediate Similarity	NPC469628
0.766	Intermediate Similarity	NPC230800
0.766	Intermediate Similarity	NPC473291
0.7654	Intermediate Similarity	NPC129665
0.7654	Intermediate Similarity	NPC477084
0.7647	Intermediate Similarity	NPC471740
0.7647	Intermediate Similarity	NPC471537
0.7647	Intermediate Similarity	NPC270126
0.7647	Intermediate Similarity	NPC308545
0.7647	Intermediate Similarity	NPC82488
0.7647	Intermediate Similarity	NPC622
0.7647	Intermediate Similarity	NPC276647
0.764	Intermediate Similarity	NPC469676
0.764	Intermediate Similarity	NPC116575
0.764	Intermediate Similarity	NPC122502
0.7634	Intermediate Similarity	NPC38830
0.7634	Intermediate Similarity	NPC471147
0.7625	Intermediate Similarity	NPC329656
0.7625	Intermediate Similarity	NPC269841
0.7625	Intermediate Similarity	NPC107130
0.7619	Intermediate Similarity	NPC281296
0.7619	Intermediate Similarity	NPC476794
0.7619	Intermediate Similarity	NPC470240
0.7619	Intermediate Similarity	NPC141789
0.7619	Intermediate Similarity	NPC171204
0.7619	Intermediate Similarity	NPC476028
0.7619	Intermediate Similarity	NPC65603
0.7614	Intermediate Similarity	NPC115786
0.7609	Intermediate Similarity	NPC150978
0.7609	Intermediate Similarity	NPC74103
0.7609	Intermediate Similarity	NPC261607
0.7609	Intermediate Similarity	NPC123177
0.7609	Intermediate Similarity	NPC111114
0.7609	Intermediate Similarity	NPC70595
0.7609	Intermediate Similarity	NPC300312
0.7609	Intermediate Similarity	NPC476705
0.759	Intermediate Similarity	NPC199445
0.759	Intermediate Similarity	NPC474419
0.759	Intermediate Similarity	NPC475861
0.759	Intermediate Similarity	NPC329826
0.759	Intermediate Similarity	NPC469414
0.7582	Intermediate Similarity	NPC471342
0.7582	Intermediate Similarity	NPC151770
0.7582	Intermediate Similarity	NPC469866
0.7582	Intermediate Similarity	NPC284561
0.7579	Intermediate Similarity	NPC471140
0.7556	Intermediate Similarity	NPC72513
0.7556	Intermediate Similarity	NPC475703
0.7556	Intermediate Similarity	NPC471738
0.7553	Intermediate Similarity	NPC475659
0.7553	Intermediate Similarity	NPC107476
0.7551	Intermediate Similarity	NPC474166
0.7551	Intermediate Similarity	NPC19239
0.7531	Intermediate Similarity	NPC472017
0.7528	Intermediate Similarity	NPC96621
0.7528	Intermediate Similarity	NPC255307
0.7528	Intermediate Similarity	NPC165162
0.7528	Intermediate Similarity	NPC99395
0.7528	Intermediate Similarity	NPC197903
0.7527	Intermediate Similarity	NPC165383
0.7527	Intermediate Similarity	NPC475838
0.7527	Intermediate Similarity	NPC125674
0.7527	Intermediate Similarity	NPC475302
0.7527	Intermediate Similarity	NPC228451
0.7526	Intermediate Similarity	NPC474339
0.7526	Intermediate Similarity	NPC164598
0.75	Intermediate Similarity	NPC469368
0.75	Intermediate Similarity	NPC235906
0.75	Intermediate Similarity	NPC222358
0.75	Intermediate Similarity	NPC474527
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC469514
0.75	Intermediate Similarity	NPC471726
0.75	Intermediate Similarity	NPC473448
0.75	Intermediate Similarity	NPC470188
0.75	Intermediate Similarity	NPC208233
0.75	Intermediate Similarity	NPC469718
0.75	Intermediate Similarity	NPC329857
0.75	Intermediate Similarity	NPC161855
0.7475	Intermediate Similarity	NPC474741
0.7475	Intermediate Similarity	NPC477510
0.7475	Intermediate Similarity	NPC471143
0.7474	Intermediate Similarity	NPC172998
0.7474	Intermediate Similarity	NPC299396
0.7474	Intermediate Similarity	NPC301596
0.7474	Intermediate Similarity	NPC473859
0.7474	Intermediate Similarity	NPC476275
0.7474	Intermediate Similarity	NPC476315
0.7473	Intermediate Similarity	NPC476707
0.7473	Intermediate Similarity	NPC476803
0.7473	Intermediate Similarity	NPC476805
0.7473	Intermediate Similarity	NPC476706
0.7471	Intermediate Similarity	NPC255580
0.7471	Intermediate Similarity	NPC39411
0.7471	Intermediate Similarity	NPC52861
0.747	Intermediate Similarity	NPC294434
0.747	Intermediate Similarity	NPC259599
0.747	Intermediate Similarity	NPC476355
0.747	Intermediate Similarity	NPC117746
0.747	Intermediate Similarity	NPC15499
0.7451	Intermediate Similarity	NPC281624
0.7449	Intermediate Similarity	NPC478156
0.7449	Intermediate Similarity	NPC475091
0.7447	Intermediate Similarity	NPC167219
0.7447	Intermediate Similarity	NPC470697
0.7447	Intermediate Similarity	NPC473316

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 NPC475989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1897
0.2-0.3	3786
0.3-0.4	2169
0.4-0.5	800
0.5-0.6	235
0.6-0.7	34
0.7-0.8	10
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
0.7586	Intermediate Similarity	NPD5209	Approved
0.7391	Intermediate Similarity	NPD1695	Approved
0.7381	Intermediate Similarity	NPD8039	Approved
0.7342	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5778	Approved
0.734	Intermediate Similarity	NPD5779	Approved
0.7312	Intermediate Similarity	NPD46	Approved
0.7312	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD5369	Approved
0.7234	Intermediate Similarity	NPD7983	Approved
0.7204	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6101	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7191	Intermediate Similarity	NPD4270	Approved
0.7188	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5785	Approved
0.7128	Intermediate Similarity	NPD7838	Discovery
0.7115	Intermediate Similarity	NPD6371	Approved
0.7065	Intermediate Similarity	NPD5786	Approved
0.7053	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4252	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7154	Phase 3
0.6778	Remote Similarity	NPD4819	Approved
0.6778	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD4820	Approved
0.6778	Remote Similarity	NPD5368	Approved
0.6778	Remote Similarity	NPD4822	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7839	Suspended
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5362	Discontinued
0.6733	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD6399	Phase 3
0.6566	Remote Similarity	NPD5282	Discontinued
0.6566	Remote Similarity	NPD7900	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6531	Remote Similarity	NPD7637	Suspended
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4225	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD6672	Approved
0.6386	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8513	Phase 3
0.6348	Remote Similarity	NPD8515	Approved
0.6348	Remote Similarity	NPD8516	Approved
0.6348	Remote Similarity	NPD8517	Approved
0.6346	Remote Similarity	NPD5344	Discontinued
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6051	Approved
0.6327	Remote Similarity	NPD5370	Suspended
0.6296	Remote Similarity	NPD6686	Approved
0.6289	Remote Similarity	NPD4251	Approved
0.6289	Remote Similarity	NPD4250	Approved
0.6273	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8273	Phase 1
0.6263	Remote Similarity	NPD5692	Phase 3
0.6263	Remote Similarity	NPD5207	Approved
0.6262	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD6053	Discontinued
0.6214	Remote Similarity	NPD6083	Phase 2
0.6214	Remote Similarity	NPD6084	Phase 2
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD5284	Approved
0.62	Remote Similarity	NPD5694	Approved
0.62	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6098	Approved
0.6186	Remote Similarity	NPD4249	Approved
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5695	Phase 3
0.617	Remote Similarity	NPD4790	Discontinued
0.6162	Remote Similarity	NPD6080	Approved
0.6162	Remote Similarity	NPD6904	Approved
0.6162	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6147	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6105	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6927	Phase 3
0.6095	Remote Similarity	NPD7639	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6413	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4756	Discovery
0.6083	Remote Similarity	NPD8074	Phase 3
0.6047	Remote Similarity	NPD7331	Phase 2
0.604	Remote Similarity	NPD7515	Phase 2
0.6024	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6422	Discontinued
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD6899	Approved
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7829	Approved
0.5966	Remote Similarity	NPD7642	Approved
0.5966	Remote Similarity	NPD7830	Approved
0.596	Remote Similarity	NPD3573	Approved
0.595	Remote Similarity	NPD8448	Approved
0.5932	Remote Similarity	NPD8444	Approved
0.593	Remote Similarity	NPD7341	Phase 2
0.5922	Remote Similarity	NPD6001	Approved
0.5909	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD5959	Approved
0.59	Remote Similarity	NPD5208	Approved
0.5897	Remote Similarity	NPD28	Approved
0.5897	Remote Similarity	NPD29	Approved
0.5893	Remote Similarity	NPD2067	Discontinued
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5882	Remote Similarity	NPD8035	Phase 2
0.5882	Remote Similarity	NPD8034	Phase 2
0.5876	Remote Similarity	NPD6695	Phase 3
0.5865	Remote Similarity	NPD5654	Approved
0.5859	Remote Similarity	NPD5279	Phase 3
0.5851	Remote Similarity	NPD3732	Approved
0.5842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5816	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4786	Approved
0.5814	Remote Similarity	NPD3197	Phase 1
0.581	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD8392	Approved
0.5806	Remote Similarity	NPD8390	Approved
0.5806	Remote Similarity	NPD8391	Approved
0.5804	Remote Similarity	NPD6013	Approved
0.5804	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD6014	Approved
0.5795	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD8297	Approved
0.5785	Remote Similarity	NPD8340	Approved
0.5785	Remote Similarity	NPD8341	Approved
0.5785	Remote Similarity	NPD8299	Approved
0.5785	Remote Similarity	NPD8342	Approved
0.5784	Remote Similarity	NPD3673	Approved
0.5784	Remote Similarity	NPD3672	Approved
0.5781	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6647	Phase 2
0.5773	Remote Similarity	NPD3667	Approved
0.5766	Remote Similarity	NPD6685	Approved
0.5747	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.573	Remote Similarity	NPD229	Approved
0.5726	Remote Similarity	NPD7319	Approved
0.5726	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.57	Remote Similarity	NPD3618	Phase 1
0.57	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4753	Phase 2
0.5684	Remote Similarity	NPD4802	Phase 2
0.5684	Remote Similarity	NPD4238	Approved
0.568	Remote Similarity	NPD6085	Phase 2
0.568	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3196	Approved
0.5679	Remote Similarity	NPD3195	Phase 2
0.5679	Remote Similarity	NPD4266	Approved
0.5679	Remote Similarity	NPD3194	Approved
0.5664	Remote Similarity	NPD2182	Approved
0.566	Remote Similarity	NPD4228	Discovery
0.5657	Remote Similarity	NPD3133	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