NPASS Compound

Structure

NPC270013 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 4.7662 -2.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0444 -5.8579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2879 -1.9824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -4.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7941 -0.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 -3.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4743 -1.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -4.7943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8632 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 -0.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 -4.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7123 -2.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7124 -2.8151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2626 -4.5037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4176 -3.7706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0355 -3.7464 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 2.2707 -1.5133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3008 -5.3299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9910 -4.0412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2353 -4.3463 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 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 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 9 1 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 18 24 1 6 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 11 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	362.212
LogP:	2.219
LogD:	2.327
LogS:	-4.149
# Rotatable Bonds:	1
TPSA:	79.29
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.214
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.76
MDCK Permeability:	2.2865813662065193e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.437
Plasma Protein Binding (PPB):	90.71845245361328%
Volume Distribution (VD):	1.27
Pgp-substrate:	3.834022283554077%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.237
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	9.524
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.848
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.948
Carcinogencity:	0.056
Eye Corrosion:	0.083
Eye Irritation:	0.111
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: NPC270013

Natural Product ID:	NPC270013
*Common Name:**	Sinularolide C
IUPAC Name:	n.a.
Synonyms:	Sinularolide C
Standard InCHIKey:	MULWDJOXRRXULO-XJFSRSTNSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-12-6-4-8-13(2)17(22)18-15(14(3)19(23)24-18)10-16-20(11-21,25-16)9-5-7-12/h7-8,15-18,21-22H,3-6,9-11H2,1-2H3/b12-7+,13-8+/t15-,16-,17+,18-,20+/m1/s1
SMILES:	OC[C@]12CC/C=C(C)/CC/C=C(/[C@@H]([C@H]3[C@H](C[C@H]2O1)C(=C)C(=O)O3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513426
PubChem CID:	11473507
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	south china sea	n.a.	PMID[18512986]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973388]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548852]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25026	Sinularia gibberosa	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
IC50	3
Others	1

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI	=	63.8	%	PMID[553262]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5.1	ug.mL-1	PMID[553263]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	5.2	ug.mL-1	PMID[553263]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	7.7	ug.mL-1	PMID[553263]

☑ 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 NPC270013 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	211
0.1-0.2	1268
0.2-0.3	4469
0.3-0.4	8209
0.4-0.5	14795
0.5-0.6	7684
0.6-0.7	4245
0.7-0.8	1486
0.8-0.85	223
0.85-0.9	66
0.9-0.95	32
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC14961
0.9886	High Similarity	NPC474035
0.9886	High Similarity	NPC81386
0.9773	High Similarity	NPC212486
0.9773	High Similarity	NPC475912
0.9667	High Similarity	NPC476315
0.9556	High Similarity	NPC36954
0.9444	High Similarity	NPC303942
0.9444	High Similarity	NPC57405
0.9438	High Similarity	NPC184463
0.9438	High Similarity	NPC30515
0.9355	High Similarity	NPC288876
0.9333	High Similarity	NPC179746
0.9333	High Similarity	NPC476300
0.9333	High Similarity	NPC81419
0.9326	High Similarity	NPC474761
0.9326	High Similarity	NPC476004
0.9326	High Similarity	NPC51004
0.9318	High Similarity	NPC202672
0.9247	High Similarity	NPC473326
0.9247	High Similarity	NPC474213
0.9239	High Similarity	NPC473859
0.9239	High Similarity	NPC279621
0.9222	High Similarity	NPC12172
0.9222	High Similarity	NPC208886
0.9213	High Similarity	NPC307411
0.9205	High Similarity	NPC231889
0.913	High Similarity	NPC475659
0.9121	High Similarity	NPC475838
0.9121	High Similarity	NPC228451
0.9121	High Similarity	NPC125674
0.9111	High Similarity	NPC475748
0.9072	High Similarity	NPC243998
0.9053	High Similarity	NPC476270
0.9022	High Similarity	NPC474247
0.9011	High Similarity	NPC473321
0.9	High Similarity	NPC474032
0.9	High Similarity	NPC151770
0.8977	High Similarity	NPC21469
0.8913	High Similarity	NPC295204
0.8913	High Similarity	NPC288240
0.8913	High Similarity	NPC273579
0.8913	High Similarity	NPC162205
0.8901	High Similarity	NPC473619
0.8889	High Similarity	NPC281516
0.8889	High Similarity	NPC473715
0.8889	High Similarity	NPC153805
0.8878	High Similarity	NPC223450
0.8854	High Similarity	NPC473332
0.8842	High Similarity	NPC187268
0.883	High Similarity	NPC230800
0.8817	High Similarity	NPC473316
0.8817	High Similarity	NPC473330
0.8804	High Similarity	NPC70251
0.8804	High Similarity	NPC475881
0.8791	High Similarity	NPC166919
0.8791	High Similarity	NPC295312
0.8788	High Similarity	NPC477513
0.8778	High Similarity	NPC186148
0.8776	High Similarity	NPC474741
0.8776	High Similarity	NPC100487
0.8764	High Similarity	NPC137033
0.8764	High Similarity	NPC47958
0.8764	High Similarity	NPC149725
0.8764	High Similarity	NPC304509
0.8763	High Similarity	NPC471148
0.875	High Similarity	NPC475949
0.875	High Similarity	NPC272814
0.8723	High Similarity	NPC107476
0.8723	High Similarity	NPC471142
0.8723	High Similarity	NPC471141
0.8696	High Similarity	NPC475855
0.8681	High Similarity	NPC58219
0.8681	High Similarity	NPC227379
0.8681	High Similarity	NPC474471
0.8681	High Similarity	NPC177629
0.8673	High Similarity	NPC475871
0.8673	High Similarity	NPC475945
0.8667	High Similarity	NPC50637
0.866	High Similarity	NPC164598
0.866	High Similarity	NPC201718
0.866	High Similarity	NPC474339
0.8652	High Similarity	NPC474780
0.8646	High Similarity	NPC471144
0.8632	High Similarity	NPC477921
0.8617	High Similarity	NPC71589
0.8617	High Similarity	NPC471147
0.8587	High Similarity	NPC92974
0.8571	High Similarity	NPC149371
0.8571	High Similarity	NPC248602
0.8571	High Similarity	NPC86077
0.8571	High Similarity	NPC474747
0.8571	High Similarity	NPC475703
0.8571	High Similarity	NPC5130
0.8557	High Similarity	NPC475053
0.8556	High Similarity	NPC38468
0.8556	High Similarity	NPC319795
0.8556	High Similarity	NPC50362
0.8556	High Similarity	NPC255307
0.8542	High Similarity	NPC40812
0.8539	High Similarity	NPC250315
0.8539	High Similarity	NPC11620
0.8526	High Similarity	NPC477922
0.8526	High Similarity	NPC304886
0.8523	High Similarity	NPC141810
0.85	High Similarity	NPC54737
0.8495	Intermediate Similarity	NPC179394
0.8495	Intermediate Similarity	NPC144133
0.8495	Intermediate Similarity	NPC473448
0.8485	Intermediate Similarity	NPC472755
0.8469	Intermediate Similarity	NPC110443
0.8469	Intermediate Similarity	NPC150923
0.8469	Intermediate Similarity	NPC46998
0.8469	Intermediate Similarity	NPC185141
0.8469	Intermediate Similarity	NPC128733
0.8469	Intermediate Similarity	NPC133907
0.8469	Intermediate Similarity	NPC47880
0.8469	Intermediate Similarity	NPC474742
0.8462	Intermediate Similarity	NPC305475
0.8462	Intermediate Similarity	NPC122502
0.8462	Intermediate Similarity	NPC475019
0.8462	Intermediate Similarity	NPC475461
0.8462	Intermediate Similarity	NPC474949
0.8462	Intermediate Similarity	NPC470242
0.8454	Intermediate Similarity	NPC279561
0.8454	Intermediate Similarity	NPC83895
0.8454	Intermediate Similarity	NPC187761
0.8444	Intermediate Similarity	NPC70424
0.8444	Intermediate Similarity	NPC151176
0.8444	Intermediate Similarity	NPC72464
0.8444	Intermediate Similarity	NPC3464
0.8444	Intermediate Similarity	NPC114979
0.8444	Intermediate Similarity	NPC243618
0.8444	Intermediate Similarity	NPC475963
0.8444	Intermediate Similarity	NPC191476
0.8421	Intermediate Similarity	NPC190294
0.8421	Intermediate Similarity	NPC474338
0.8421	Intermediate Similarity	NPC140543
0.8404	Intermediate Similarity	NPC470373
0.8404	Intermediate Similarity	NPC20713
0.8404	Intermediate Similarity	NPC476705
0.8404	Intermediate Similarity	NPC470379
0.84	Intermediate Similarity	NPC203659
0.8387	Intermediate Similarity	NPC473564
0.8384	Intermediate Similarity	NPC320019
0.8384	Intermediate Similarity	NPC324017
0.837	Intermediate Similarity	NPC179659
0.837	Intermediate Similarity	NPC160138
0.837	Intermediate Similarity	NPC474765
0.8352	Intermediate Similarity	NPC329749
0.8352	Intermediate Similarity	NPC165162
0.835	Intermediate Similarity	NPC5103
0.8333	Intermediate Similarity	NPC473390
0.8333	Intermediate Similarity	NPC474947
0.8333	Intermediate Similarity	NPC131669
0.8316	Intermediate Similarity	NPC469692
0.8316	Intermediate Similarity	NPC469645
0.83	Intermediate Similarity	NPC110989
0.8298	Intermediate Similarity	NPC474323
0.8298	Intermediate Similarity	NPC312042
0.8298	Intermediate Similarity	NPC49342
0.8298	Intermediate Similarity	NPC469368
0.8298	Intermediate Similarity	NPC62815
0.8298	Intermediate Similarity	NPC474232
0.8298	Intermediate Similarity	NPC469718
0.8298	Intermediate Similarity	NPC251385
0.8298	Intermediate Similarity	NPC329857
0.8298	Intermediate Similarity	NPC206614
0.8295	Intermediate Similarity	NPC617
0.8283	Intermediate Similarity	NPC477511
0.8283	Intermediate Similarity	NPC264477
0.8283	Intermediate Similarity	NPC15993
0.8283	Intermediate Similarity	NPC472753
0.828	Intermediate Similarity	NPC476803
0.828	Intermediate Similarity	NPC476704
0.8265	Intermediate Similarity	NPC221615
0.8265	Intermediate Similarity	NPC222303
0.8265	Intermediate Similarity	NPC261377
0.8265	Intermediate Similarity	NPC308567
0.8265	Intermediate Similarity	NPC208233
0.8265	Intermediate Similarity	NPC255592
0.8261	Intermediate Similarity	NPC474762
0.8261	Intermediate Similarity	NPC164393
0.8261	Intermediate Similarity	NPC284902
0.8261	Intermediate Similarity	NPC112685
0.8261	Intermediate Similarity	NPC476015
0.8261	Intermediate Similarity	NPC469910
0.8252	Intermediate Similarity	NPC59489
0.8252	Intermediate Similarity	NPC38154
0.8252	Intermediate Similarity	NPC139838
0.8247	Intermediate Similarity	NPC35498
0.8247	Intermediate Similarity	NPC39859
0.8247	Intermediate Similarity	NPC76862
0.8247	Intermediate Similarity	NPC470883
0.8247	Intermediate Similarity	NPC158416
0.8247	Intermediate Similarity	NPC476009
0.8247	Intermediate Similarity	NPC17585
0.8242	Intermediate Similarity	NPC9868
0.8242	Intermediate Similarity	NPC96259
0.8242	Intermediate Similarity	NPC476804

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 NPC270013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1865
0.2-0.3	3650
0.3-0.4	2252
0.4-0.5	757
0.5-0.6	320
0.6-0.7	91
0.7-0.8	13
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD1733	Clinical (unspecified phase)
0.8495	Intermediate Similarity	NPD6698	Approved
0.8495	Intermediate Similarity	NPD46	Approved
0.8105	Intermediate Similarity	NPD7838	Discovery
0.8021	Intermediate Similarity	NPD7983	Approved
0.8	Intermediate Similarity	NPD6371	Approved
0.7885	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1695	Approved
0.76	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5344	Discontinued
0.7379	Intermediate Similarity	NPD4225	Approved
0.7379	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6686	Approved
0.7228	Intermediate Similarity	NPD5778	Approved
0.7228	Intermediate Similarity	NPD5779	Approved
0.7188	Intermediate Similarity	NPD7154	Phase 3
0.7155	Intermediate Similarity	NPD8517	Approved
0.7155	Intermediate Similarity	NPD8515	Approved
0.7155	Intermediate Similarity	NPD8513	Phase 3
0.7155	Intermediate Similarity	NPD8516	Approved
0.7143	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD4249	Approved
0.7105	Intermediate Similarity	NPD7115	Discovery
0.7091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4250	Approved
0.7071	Intermediate Similarity	NPD4251	Approved
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.703	Intermediate Similarity	NPD5785	Approved
0.697	Remote Similarity	NPD5786	Approved
0.6907	Remote Similarity	NPD6435	Approved
0.6891	Remote Similarity	NPD7642	Approved
0.6875	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4819	Approved
0.6875	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4822	Approved
0.6875	Remote Similarity	NPD4820	Approved
0.6875	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5363	Approved
0.686	Remote Similarity	NPD8074	Phase 3
0.6857	Remote Similarity	NPD7839	Suspended
0.6837	Remote Similarity	NPD5362	Discontinued
0.6827	Remote Similarity	NPD5282	Discontinued
0.675	Remote Similarity	NPD7830	Approved
0.675	Remote Similarity	NPD7829	Approved
0.6735	Remote Similarity	NPD4270	Approved
0.6735	Remote Similarity	NPD4269	Approved
0.6701	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6639	Remote Similarity	NPD8273	Phase 1
0.6639	Remote Similarity	NPD7507	Approved
0.6633	Remote Similarity	NPD5369	Approved
0.6629	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6101	Approved
0.6574	Remote Similarity	NPD7638	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4632	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1694	Approved
0.6531	Remote Similarity	NPD4252	Approved
0.6512	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8451	Approved
0.65	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD6110	Phase 1
0.6495	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD7641	Discontinued
0.6452	Remote Similarity	NPD8448	Approved
0.6423	Remote Similarity	NPD8340	Approved
0.6423	Remote Similarity	NPD8341	Approved
0.6423	Remote Similarity	NPD8342	Approved
0.6423	Remote Similarity	NPD8299	Approved
0.6337	Remote Similarity	NPD5331	Approved
0.6337	Remote Similarity	NPD5332	Approved
0.6325	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD7637	Suspended
0.6316	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD8444	Approved
0.6304	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4790	Discontinued
0.6299	Remote Similarity	NPD8390	Approved
0.6299	Remote Similarity	NPD8391	Approved
0.6299	Remote Similarity	NPD8392	Approved
0.629	Remote Similarity	NPD7492	Approved
0.6275	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6399	Phase 3
0.6261	Remote Similarity	NPD6899	Approved
0.6261	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD6009	Approved
0.624	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD2204	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6238	Remote Similarity	NPD5209	Approved
0.623	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD6402	Approved
0.6228	Remote Similarity	NPD6675	Approved
0.6228	Remote Similarity	NPD5739	Approved
0.6228	Remote Similarity	NPD7128	Approved
0.621	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6372	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.6207	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD7078	Approved
0.6179	Remote Similarity	NPD6015	Approved
0.6179	Remote Similarity	NPD6016	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6174	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD6421	Discontinued
0.6142	Remote Similarity	NPD7736	Approved
0.6134	Remote Similarity	NPD8133	Approved
0.6132	Remote Similarity	NPD5370	Suspended
0.6129	Remote Similarity	NPD6370	Approved
0.6129	Remote Similarity	NPD5988	Approved
0.6121	Remote Similarity	NPD7320	Approved
0.6121	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7632	Discontinued
0.6106	Remote Similarity	NPD5211	Phase 2
0.6102	Remote Similarity	NPD8130	Phase 1
0.6102	Remote Similarity	NPD6869	Approved
0.6102	Remote Similarity	NPD6617	Approved
0.6102	Remote Similarity	NPD6847	Approved
0.6098	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6845	Suspended
0.6066	Remote Similarity	NPD7328	Approved
0.6066	Remote Similarity	NPD7327	Approved
0.6063	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD4756	Discovery
0.605	Remote Similarity	NPD6882	Approved
0.6048	Remote Similarity	NPD8033	Approved
0.6048	Remote Similarity	NPD7503	Approved
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD7331	Phase 2
0.602	Remote Similarity	NPD8039	Approved
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6695	Phase 3
0.6017	Remote Similarity	NPD4634	Approved
0.6016	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD6422	Discontinued
0.5984	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD7500	Approved
0.5984	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5696	Approved
0.5978	Remote Similarity	NPD3197	Phase 1
0.5968	Remote Similarity	NPD8294	Approved
0.5968	Remote Similarity	NPD8377	Approved
0.5966	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.594	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4696	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5926	Remote Similarity	NPD3168	Discontinued
0.592	Remote Similarity	NPD8335	Approved
0.592	Remote Similarity	NPD8378	Approved
0.592	Remote Similarity	NPD8268	Approved
0.592	Remote Similarity	NPD8266	Approved
0.592	Remote Similarity	NPD8269	Approved
0.592	Remote Similarity	NPD8379	Approved
0.592	Remote Similarity	NPD6921	Approved
0.592	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8267	Approved
0.592	Remote Similarity	NPD8296	Approved
0.592	Remote Similarity	NPD8380	Approved
0.5914	Remote Similarity	NPD7341	Phase 2
0.5902	Remote Similarity	NPD6274	Approved
0.5893	Remote Similarity	NPD7902	Approved
0.5893	Remote Similarity	NPD4755	Approved
0.5854	Remote Similarity	NPD7505	Discontinued
0.5833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5225	Approved
0.5826	Remote Similarity	NPD5226	Approved
0.5826	Remote Similarity	NPD4633	Approved
0.5826	Remote Similarity	NPD5224	Approved
0.5812	Remote Similarity	NPD5048	Discontinued

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