NPASS Compound

Structure

NPC473603 OpenBabel07101719252D 29 29 0 0 1 0 0 0 0 0999 V2000 -6.1324 -1.1807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4718 2.4270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2937 -1.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4027 -1.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5640 -1.8160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6730 -1.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8343 -1.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9433 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2677 0.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5036 2.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8030 2.8905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2359 1.2135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 20 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 21 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 26 2 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	440.6
LogP:	3.95
LogD:	3.813
LogS:	-4.47
# Rotatable Bonds:	15
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	3.807
Fsp3:	0.542
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:	-4.685
MDCK Permeability:	2.8201275199535303e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.93
Plasma Protein Binding (PPB):	96.91661834716797%
Volume Distribution (VD):	1.274
Pgp-substrate:	3.077331066131592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.839
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.654
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	3.251
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.301
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.925
Carcinogencity:	0.824
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC473603

Natural Product ID:	NPC473603
*Common Name:**	Claviridenone F
IUPAC Name:	methyl (Z,7E)-7-[2-(acetyloxymethyl)-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate
Synonyms:	Claviridenone F
Standard InCHIKey:	FFJWZZQBWBDIJB-WDNHCDEGSA-N
Standard InCHI:	InChI=1S/C24H34O5/c1-4-5-6-7-10-13-17-24(19-29-20(2)25)18-16-22(26)21(24)14-11-8-9-12-15-23(27)28-3/h8,10-11,13-14,16,18H,4-7,9,12,15,17,19H2,1-3H3/b11-8-,13-10-,21-14-
SMILES:	CCCCCC=CCC1(C=CC(=O)C1=CC=CCCCC(=O)OC)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446975
PubChem CID:	44575979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001722] Fatty alcohol esters

*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
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11720524]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO33409	clavularia violacea	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Taiwanese octocoral	n.a.	PMID[15104481]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.0	10'-3 ug/ml	PMID[571144]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.1	10'-2 ug/ml	PMID[571144]
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.2	10'-7 ug/ml	PMID[571144]

☑ 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 NPC473603 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	177
0.1-0.2	1581
0.2-0.3	9309
0.3-0.4	17233
0.4-0.5	8491
0.5-0.6	4867
0.6-0.7	974
0.7-0.8	62
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476059
0.8451	Intermediate Similarity	NPC287878
0.7945	Intermediate Similarity	NPC238948
0.7945	Intermediate Similarity	NPC215745
0.7945	Intermediate Similarity	NPC12815
0.7941	Intermediate Similarity	NPC322457
0.7681	Intermediate Similarity	NPC474658
0.7671	Intermediate Similarity	NPC318766
0.7639	Intermediate Similarity	NPC470256
0.7632	Intermediate Similarity	NPC4492
0.7632	Intermediate Similarity	NPC51391
0.7534	Intermediate Similarity	NPC476591
0.7534	Intermediate Similarity	NPC88877
0.75	Intermediate Similarity	NPC203335
0.75	Intermediate Similarity	NPC21998
0.75	Intermediate Similarity	NPC194871
0.7432	Intermediate Similarity	NPC469660
0.7403	Intermediate Similarity	NPC27205
0.7403	Intermediate Similarity	NPC472967
0.7403	Intermediate Similarity	NPC266159
0.7375	Intermediate Similarity	NPC474980
0.7375	Intermediate Similarity	NPC275507
0.7375	Intermediate Similarity	NPC42470
0.7368	Intermediate Similarity	NPC259599
0.7368	Intermediate Similarity	NPC476355
0.7368	Intermediate Similarity	NPC294434
0.7368	Intermediate Similarity	NPC15499
0.7368	Intermediate Similarity	NPC117746
0.7368	Intermediate Similarity	NPC140287
0.7342	Intermediate Similarity	NPC63649
0.7342	Intermediate Similarity	NPC264227
0.7342	Intermediate Similarity	NPC471299
0.7342	Intermediate Similarity	NPC472965
0.7342	Intermediate Similarity	NPC265980
0.7342	Intermediate Similarity	NPC63326
0.7333	Intermediate Similarity	NPC257618
0.7297	Intermediate Similarity	NPC470693
0.7286	Intermediate Similarity	NPC151648
0.7237	Intermediate Similarity	NPC276336
0.7222	Intermediate Similarity	NPC470688
0.7215	Intermediate Similarity	NPC253749
0.7195	Intermediate Similarity	NPC16488
0.7183	Intermediate Similarity	NPC155849
0.7179	Intermediate Similarity	NPC123360
0.716	Intermediate Similarity	NPC471325
0.7143	Intermediate Similarity	NPC143857
0.7143	Intermediate Similarity	NPC474758
0.7143	Intermediate Similarity	NPC79756
0.7143	Intermediate Similarity	NPC229252
0.7125	Intermediate Similarity	NPC158565
0.7125	Intermediate Similarity	NPC270126
0.7125	Intermediate Similarity	NPC178277
0.7123	Intermediate Similarity	NPC248125
0.7121	Intermediate Similarity	NPC37644
0.7108	Intermediate Similarity	NPC38569
0.7108	Intermediate Similarity	NPC163615
0.7105	Intermediate Similarity	NPC316185
0.7105	Intermediate Similarity	NPC163003
0.7105	Intermediate Similarity	NPC67076
0.7105	Intermediate Similarity	NPC319163
0.7089	Intermediate Similarity	NPC97516
0.7089	Intermediate Similarity	NPC57744
0.7089	Intermediate Similarity	NPC473825
0.7073	Intermediate Similarity	NPC26624
0.7073	Intermediate Similarity	NPC94200
0.7067	Intermediate Similarity	NPC236208
0.7059	Intermediate Similarity	NPC252860
0.7042	Intermediate Similarity	NPC228574
0.7042	Intermediate Similarity	NPC294304
0.7037	Intermediate Similarity	NPC160582
0.7027	Intermediate Similarity	NPC106613
0.7024	Intermediate Similarity	NPC21471
0.7024	Intermediate Similarity	NPC470177
0.7024	Intermediate Similarity	NPC161957
0.7024	Intermediate Similarity	NPC33570
0.7024	Intermediate Similarity	NPC155873
0.7015	Intermediate Similarity	NPC322461
0.7013	Intermediate Similarity	NPC222244
0.7013	Intermediate Similarity	NPC472956
0.7013	Intermediate Similarity	NPC16349
0.7013	Intermediate Similarity	NPC470237
0.7011	Intermediate Similarity	NPC475965
0.7011	Intermediate Similarity	NPC474842
0.7	Intermediate Similarity	NPC279532
0.7	Intermediate Similarity	NPC108816
0.7	Intermediate Similarity	NPC93763
0.7	Intermediate Similarity	NPC128276
0.6988	Remote Similarity	NPC108045
0.6988	Remote Similarity	NPC475622
0.6988	Remote Similarity	NPC118423
0.6986	Remote Similarity	NPC131174
0.6986	Remote Similarity	NPC220766
0.6986	Remote Similarity	NPC133904
0.6974	Remote Similarity	NPC475310
0.697	Remote Similarity	NPC170167
0.6951	Remote Similarity	NPC286229
0.6951	Remote Similarity	NPC255580
0.6951	Remote Similarity	NPC39411
0.6944	Remote Similarity	NPC210303
0.6944	Remote Similarity	NPC44343
0.6944	Remote Similarity	NPC474774
0.6944	Remote Similarity	NPC179087
0.6941	Remote Similarity	NPC70555
0.6941	Remote Similarity	NPC315395
0.6941	Remote Similarity	NPC104961
0.6941	Remote Similarity	NPC316426
0.6941	Remote Similarity	NPC70422
0.6941	Remote Similarity	NPC168248
0.6932	Remote Similarity	NPC150978
0.6932	Remote Similarity	NPC123177
0.6932	Remote Similarity	NPC70595
0.6932	Remote Similarity	NPC74103
0.6923	Remote Similarity	NPC227396
0.6923	Remote Similarity	NPC476590
0.6923	Remote Similarity	NPC107654
0.6923	Remote Similarity	NPC114727
0.6923	Remote Similarity	NPC315843
0.6923	Remote Similarity	NPC160540
0.6914	Remote Similarity	NPC469620
0.6914	Remote Similarity	NPC469690
0.6905	Remote Similarity	NPC474865
0.6905	Remote Similarity	NPC31086
0.6905	Remote Similarity	NPC115786
0.6897	Remote Similarity	NPC284561
0.6897	Remote Similarity	NPC474844
0.6892	Remote Similarity	NPC191233
0.6875	Remote Similarity	NPC470240
0.6875	Remote Similarity	NPC15975
0.6875	Remote Similarity	NPC68156
0.6875	Remote Similarity	NPC476794
0.6875	Remote Similarity	NPC195785
0.6875	Remote Similarity	NPC476028
0.6875	Remote Similarity	NPC171204
0.6875	Remote Similarity	NPC141789
0.6867	Remote Similarity	NPC471296
0.6867	Remote Similarity	NPC268122
0.6867	Remote Similarity	NPC173609
0.6866	Remote Similarity	NPC296311
0.686	Remote Similarity	NPC473248
0.6849	Remote Similarity	NPC34883
0.6835	Remote Similarity	NPC244166
0.6835	Remote Similarity	NPC193351
0.6835	Remote Similarity	NPC169056
0.6835	Remote Similarity	NPC324762
0.6835	Remote Similarity	NPC226669
0.6835	Remote Similarity	NPC225665
0.6835	Remote Similarity	NPC260396
0.6835	Remote Similarity	NPC155587
0.6835	Remote Similarity	NPC228978
0.6835	Remote Similarity	NPC138408
0.6835	Remote Similarity	NPC166018
0.6829	Remote Similarity	NPC302426
0.6829	Remote Similarity	NPC281132
0.6829	Remote Similarity	NPC223904
0.6829	Remote Similarity	NPC304795
0.6818	Remote Similarity	NPC469372
0.6818	Remote Similarity	NPC253144
0.6818	Remote Similarity	NPC244452
0.6812	Remote Similarity	NPC325977
0.6806	Remote Similarity	NPC260573
0.6795	Remote Similarity	NPC474705
0.6795	Remote Similarity	NPC58956
0.6795	Remote Similarity	NPC144947
0.6795	Remote Similarity	NPC284006
0.6795	Remote Similarity	NPC269206
0.6795	Remote Similarity	NPC295633
0.679	Remote Similarity	NPC99182
0.679	Remote Similarity	NPC469510
0.679	Remote Similarity	NPC182292
0.679	Remote Similarity	NPC192006
0.679	Remote Similarity	NPC471220
0.679	Remote Similarity	NPC267231
0.679	Remote Similarity	NPC474005
0.6786	Remote Similarity	NPC215294
0.6786	Remote Similarity	NPC39588
0.6786	Remote Similarity	NPC474790
0.6786	Remote Similarity	NPC474976
0.6786	Remote Similarity	NPC161045
0.6782	Remote Similarity	NPC153570
0.6778	Remote Similarity	NPC477129
0.6778	Remote Similarity	NPC477130
0.6761	Remote Similarity	NPC329249
0.6757	Remote Similarity	NPC182794
0.6753	Remote Similarity	NPC472955
0.675	Remote Similarity	NPC203277
0.675	Remote Similarity	NPC40353
0.675	Remote Similarity	NPC4509
0.6747	Remote Similarity	NPC281949
0.6747	Remote Similarity	NPC301477
0.6747	Remote Similarity	NPC25684
0.6747	Remote Similarity	NPC474955
0.6744	Remote Similarity	NPC234038
0.6744	Remote Similarity	NPC107787
0.6744	Remote Similarity	NPC211892
0.6744	Remote Similarity	NPC291712
0.6742	Remote Similarity	NPC284185
0.6716	Remote Similarity	NPC216407
0.6714	Remote Similarity	NPC211752
0.6714	Remote Similarity	NPC323498
0.6714	Remote Similarity	NPC323597

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 NPC473603 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	2006
0.2-0.3	4456
0.3-0.4	1876
0.4-0.5	458
0.5-0.6	173
0.6-0.7	28
0.7-0.8	0
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
0.7722	Intermediate Similarity	NPD5209	Approved
0.6875	Remote Similarity	NPD5343	Approved
0.6835	Remote Similarity	NPD8039	Approved
0.6629	Remote Similarity	NPD5785	Approved
0.6627	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1694	Approved
0.6437	Remote Similarity	NPD5363	Approved
0.6406	Remote Similarity	NPD6097	Approved
0.6406	Remote Similarity	NPD6096	Approved
0.6404	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD6672	Approved
0.6395	Remote Similarity	NPD7154	Phase 3
0.6386	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6353	Remote Similarity	NPD5369	Approved
0.6324	Remote Similarity	NPD6927	Phase 3
0.6316	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4756	Discovery
0.6264	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD8779	Phase 3
0.6235	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4252	Approved
0.6234	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6903	Approved
0.6222	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5362	Discontinued
0.6196	Remote Similarity	NPD5694	Approved
0.6196	Remote Similarity	NPD6050	Approved
0.6196	Remote Similarity	NPD7637	Suspended
0.6196	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4193	Approved
0.6133	Remote Similarity	NPD4192	Approved
0.6133	Remote Similarity	NPD4191	Approved
0.6133	Remote Similarity	NPD4194	Approved
0.6129	Remote Similarity	NPD6399	Phase 3
0.6098	Remote Similarity	NPD4058	Approved
0.6092	Remote Similarity	NPD4270	Approved
0.6092	Remote Similarity	NPD6435	Approved
0.6092	Remote Similarity	NPD4269	Approved
0.6087	Remote Similarity	NPD7838	Discovery
0.6087	Remote Similarity	NPD5692	Phase 3
0.6064	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7900	Approved
0.6064	Remote Similarity	NPD5282	Discontinued
0.6061	Remote Similarity	NPD6647	Phase 2
0.6061	Remote Similarity	NPD3174	Discontinued
0.6022	Remote Similarity	NPD5281	Approved
0.6022	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6080	Approved
0.5978	Remote Similarity	NPD6904	Approved
0.5978	Remote Similarity	NPD6673	Approved
0.5946	Remote Similarity	NPD6109	Phase 1
0.5934	Remote Similarity	NPD3573	Approved
0.5904	Remote Similarity	NPD4687	Approved
0.5904	Remote Similarity	NPD5733	Approved
0.5895	Remote Similarity	NPD7748	Approved
0.5889	Remote Similarity	NPD1696	Phase 3
0.5889	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7902	Approved
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.5865	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD4820	Approved
0.5862	Remote Similarity	NPD4821	Approved
0.5862	Remote Similarity	NPD4819	Approved
0.5862	Remote Similarity	NPD4822	Approved
0.5862	Remote Similarity	NPD5368	Approved
0.5857	Remote Similarity	NPD29	Approved
0.5857	Remote Similarity	NPD28	Approved
0.5854	Remote Similarity	NPD5276	Approved
0.5851	Remote Similarity	NPD7983	Approved
0.5843	Remote Similarity	NPD5331	Approved
0.5843	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD9298	Approved
0.5833	Remote Similarity	NPD5695	Phase 3
0.5823	Remote Similarity	NPD7331	Phase 2
0.5821	Remote Similarity	NPD4222	Approved
0.5821	Remote Similarity	NPD39	Approved
0.5816	Remote Similarity	NPD5696	Approved
0.5816	Remote Similarity	NPD4225	Approved
0.5806	Remote Similarity	NPD5370	Suspended
0.5806	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1695	Approved
0.5797	Remote Similarity	NPD3173	Approved
0.5797	Remote Similarity	NPD4220	Pre-registration
0.5795	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD5778	Approved
0.5778	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4251	Approved
0.5761	Remote Similarity	NPD4250	Approved
0.5745	Remote Similarity	NPD46	Approved
0.5745	Remote Similarity	NPD6698	Approved
0.5732	Remote Similarity	NPD4691	Approved
0.5714	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD5208	Approved
0.5684	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5693	Phase 1
0.5684	Remote Similarity	NPD7515	Phase 2
0.5682	Remote Similarity	NPD4695	Discontinued
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.567	Remote Similarity	NPD5654	Approved
0.5667	Remote Similarity	NPD6110	Phase 1
0.566	Remote Similarity	NPD6650	Approved
0.566	Remote Similarity	NPD6649	Approved
0.5657	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5652	Remote Similarity	NPD6422	Discontinued
0.5652	Remote Similarity	NPD4249	Approved
0.5652	Remote Similarity	NPD5279	Phase 3
0.5641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6008	Approved
0.5625	Remote Similarity	NPD5783	Phase 3
0.5616	Remote Similarity	NPD4266	Approved
0.5616	Remote Similarity	NPD3196	Approved
0.5616	Remote Similarity	NPD3194	Approved
0.5616	Remote Similarity	NPD3195	Phase 2
0.5612	Remote Similarity	NPD7839	Suspended
0.561	Remote Similarity	NPD4137	Phase 3
0.56	Remote Similarity	NPD7640	Approved
0.56	Remote Similarity	NPD7639	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