NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.943
LogD:	1.426
LogS:	-2.46
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.776
Synthetic Accessibility Score:	5.188
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.481
MDCK Permeability:	2.428322477499023e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	70.74505615234375%
Volume Distribution (VD):	0.302
Pgp-substrate:	29.869083404541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	9.022
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.159
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.432
Skin Sensitization:	0.91
Carcinogencity:	0.894
Eye Corrosion:	0.923
Eye Irritation:	0.881
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC65350

Natural Product ID:	NPC65350
*Common Name:**	Subergorgic Acid
IUPAC Name:	(3R,3aS,5aS,8R,8aS)-3,5a,8-trimethyl-1-oxo-2,3,3a,4,5,8-hexahydrocyclopenta[h]pentalene-7-carboxylic acid
Synonyms:	Subergorgic acid
Standard InCHIKey:	LFKSRWRSZVCLFJ-VDHTUSMASA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-6-12(16)15-9(2)10(13(17)18)7-14(15,3)5-4-11(8)15/h7-9,11H,4-6H2,1-3H3,(H,17,18)/t8-,9+,11+,14+,15+/m1/s1
SMILES:	C[C@@H]1CC(=O)[C@]23[C@@H](C)C(=C[C@]3(C)CC[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453238
PubChem CID:	11054000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002004] Triquinane sesquiterpenoids [CHEMONTID:0003582] Angular triquinanes

*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
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10346965]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	root	n.a.	PMID[10617409]
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141096]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575966]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	Taiwanese gorgonian coral	n.a.	PMID[12088433]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	Taiwanese Gorgonian coral	n.a.	PMID[12141868]
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974612]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124781]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18290631]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26509914]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14422	Gorgoniae suberogorgia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO14422	Gorgoniae suberogorgia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29062	Hibiscus syriacus	Species	Malvaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	13.3	ug ml-1	PMID[516841]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[516841]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[516841]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[516842]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[516842]

☑ 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 NPC65350 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	181
0.1-0.2	1458
0.2-0.3	7501
0.3-0.4	15845
0.4-0.5	9159
0.5-0.6	6022
0.6-0.7	2273
0.7-0.8	247
0.8-0.85	6
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC238197
0.8605	High Similarity	NPC232747
0.8222	Intermediate Similarity	NPC90453
0.814	Intermediate Similarity	NPC142649
0.8101	Intermediate Similarity	NPC29328
0.8049	Intermediate Similarity	NPC74685
0.8023	Intermediate Similarity	NPC7927
0.8023	Intermediate Similarity	NPC230527
0.8	Intermediate Similarity	NPC20262
0.8	Intermediate Similarity	NPC256750
0.7978	Intermediate Similarity	NPC476388
0.7978	Intermediate Similarity	NPC477215
0.7975	Intermediate Similarity	NPC18543
0.7952	Intermediate Similarity	NPC169095
0.7931	Intermediate Similarity	NPC476628
0.7857	Intermediate Similarity	NPC476624
0.7857	Intermediate Similarity	NPC472013
0.7848	Intermediate Similarity	NPC67608
0.7841	Intermediate Similarity	NPC6247
0.7841	Intermediate Similarity	NPC472869
0.7831	Intermediate Similarity	NPC472014
0.7831	Intermediate Similarity	NPC97377
0.7821	Intermediate Similarity	NPC60120
0.7816	Intermediate Similarity	NPC472864
0.7816	Intermediate Similarity	NPC164577
0.7816	Intermediate Similarity	NPC472865
0.7816	Intermediate Similarity	NPC19849
0.7791	Intermediate Similarity	NPC477269
0.7791	Intermediate Similarity	NPC477271
0.7791	Intermediate Similarity	NPC129080
0.7791	Intermediate Similarity	NPC477270
0.7765	Intermediate Similarity	NPC164218
0.7753	Intermediate Similarity	NPC476409
0.7738	Intermediate Similarity	NPC476627
0.7722	Intermediate Similarity	NPC476614
0.7711	Intermediate Similarity	NPC469646
0.7701	Intermediate Similarity	NPC97913
0.7683	Intermediate Similarity	NPC206875
0.7674	Intermediate Similarity	NPC477372
0.7667	Intermediate Similarity	NPC472870
0.7667	Intermediate Similarity	NPC117122
0.766	Intermediate Similarity	NPC472941
0.766	Intermediate Similarity	NPC456
0.7647	Intermediate Similarity	NPC301769
0.7647	Intermediate Similarity	NPC32758
0.764	Intermediate Similarity	NPC186975
0.7614	Intermediate Similarity	NPC248758
0.7609	Intermediate Similarity	NPC290651
0.7604	Intermediate Similarity	NPC287833
0.7595	Intermediate Similarity	NPC476626
0.759	Intermediate Similarity	NPC472327
0.759	Intermediate Similarity	NPC474011
0.759	Intermediate Similarity	NPC251435
0.7586	Intermediate Similarity	NPC238991
0.7586	Intermediate Similarity	NPC302661
0.7582	Intermediate Similarity	NPC262043
0.7582	Intermediate Similarity	NPC170775
0.7558	Intermediate Similarity	NPC279667
0.7558	Intermediate Similarity	NPC47747
0.7558	Intermediate Similarity	NPC45495
0.7556	Intermediate Similarity	NPC236618
0.7556	Intermediate Similarity	NPC136948
0.7556	Intermediate Similarity	NPC237540
0.7529	Intermediate Similarity	NPC198240
0.7529	Intermediate Similarity	NPC192006
0.7528	Intermediate Similarity	NPC8571
0.7528	Intermediate Similarity	NPC29447
0.75	Intermediate Similarity	NPC215481
0.75	Intermediate Similarity	NPC49019
0.75	Intermediate Similarity	NPC102197
0.75	Intermediate Similarity	NPC471610
0.75	Intermediate Similarity	NPC476629
0.75	Intermediate Similarity	NPC472866
0.7473	Intermediate Similarity	NPC474854
0.747	Intermediate Similarity	NPC7382
0.7442	Intermediate Similarity	NPC477371
0.7442	Intermediate Similarity	NPC7232
0.7442	Intermediate Similarity	NPC261125
0.7442	Intermediate Similarity	NPC181195
0.7442	Intermediate Similarity	NPC84185
0.7442	Intermediate Similarity	NPC66677
0.7442	Intermediate Similarity	NPC471890
0.7439	Intermediate Similarity	NPC288667
0.7423	Intermediate Similarity	NPC51370
0.7419	Intermediate Similarity	NPC474018
0.7419	Intermediate Similarity	NPC204341
0.7419	Intermediate Similarity	NPC473986
0.7416	Intermediate Similarity	NPC475100
0.7412	Intermediate Similarity	NPC86917
0.7412	Intermediate Similarity	NPC475932
0.7412	Intermediate Similarity	NPC122264
0.7412	Intermediate Similarity	NPC61952
0.7396	Intermediate Similarity	NPC476253
0.7391	Intermediate Similarity	NPC214387
0.7391	Intermediate Similarity	NPC123912
0.7391	Intermediate Similarity	NPC268298
0.7391	Intermediate Similarity	NPC66344
0.7386	Intermediate Similarity	NPC133844
0.7386	Intermediate Similarity	NPC142253
0.7386	Intermediate Similarity	NPC3511
0.7386	Intermediate Similarity	NPC320514
0.7386	Intermediate Similarity	NPC472867
0.7386	Intermediate Similarity	NPC472239
0.7381	Intermediate Similarity	NPC77501
0.7381	Intermediate Similarity	NPC201263
0.7381	Intermediate Similarity	NPC216791
0.7381	Intermediate Similarity	NPC476795
0.7368	Intermediate Similarity	NPC472469
0.7368	Intermediate Similarity	NPC476174
0.7349	Intermediate Similarity	NPC300940
0.734	Intermediate Similarity	NPC37816
0.734	Intermediate Similarity	NPC472871
0.7333	Intermediate Similarity	NPC245434
0.7333	Intermediate Similarity	NPC94531
0.7333	Intermediate Similarity	NPC473038
0.7333	Intermediate Similarity	NPC311702
0.7333	Intermediate Similarity	NPC269638
0.7333	Intermediate Similarity	NPC123319
0.7326	Intermediate Similarity	NPC74410
0.7326	Intermediate Similarity	NPC62336
0.732	Intermediate Similarity	NPC197386
0.7312	Intermediate Similarity	NPC129419
0.7312	Intermediate Similarity	NPC476369
0.7312	Intermediate Similarity	NPC477147
0.7312	Intermediate Similarity	NPC477149
0.7312	Intermediate Similarity	NPC476437
0.7303	Intermediate Similarity	NPC310470
0.7294	Intermediate Similarity	NPC473223
0.7294	Intermediate Similarity	NPC279537
0.7294	Intermediate Similarity	NPC182848
0.7292	Intermediate Similarity	NPC29152
0.7292	Intermediate Similarity	NPC9812
0.7283	Intermediate Similarity	NPC193843
0.7283	Intermediate Similarity	NPC249889
0.7283	Intermediate Similarity	NPC477710
0.7273	Intermediate Similarity	NPC59994
0.7273	Intermediate Similarity	NPC201912
0.7273	Intermediate Similarity	NPC293753
0.7273	Intermediate Similarity	NPC78677
0.7273	Intermediate Similarity	NPC147066
0.7273	Intermediate Similarity	NPC38350
0.7273	Intermediate Similarity	NPC171665
0.7263	Intermediate Similarity	NPC167219
0.725	Intermediate Similarity	NPC126899
0.725	Intermediate Similarity	NPC322035
0.725	Intermediate Similarity	NPC142423
0.725	Intermediate Similarity	NPC154728
0.725	Intermediate Similarity	NPC308294
0.725	Intermediate Similarity	NPC100719
0.725	Intermediate Similarity	NPC166791
0.725	Intermediate Similarity	NPC304665
0.725	Intermediate Similarity	NPC162309
0.7245	Intermediate Similarity	NPC476274
0.7241	Intermediate Similarity	NPC469690
0.7241	Intermediate Similarity	NPC469617
0.7234	Intermediate Similarity	NPC111114
0.7234	Intermediate Similarity	NPC470113
0.7234	Intermediate Similarity	NPC261607
0.7234	Intermediate Similarity	NPC300312
0.7229	Intermediate Similarity	NPC21944
0.7229	Intermediate Similarity	NPC469737
0.7222	Intermediate Similarity	NPC149869
0.7222	Intermediate Similarity	NPC181743
0.7222	Intermediate Similarity	NPC472326
0.7222	Intermediate Similarity	NPC16287
0.7222	Intermediate Similarity	NPC165064
0.7222	Intermediate Similarity	NPC178025
0.7222	Intermediate Similarity	NPC87552
0.7216	Intermediate Similarity	NPC156546
0.7215	Intermediate Similarity	NPC473902
0.7209	Intermediate Similarity	NPC137547
0.7209	Intermediate Similarity	NPC103987
0.7209	Intermediate Similarity	NPC53581
0.7209	Intermediate Similarity	NPC276769
0.7209	Intermediate Similarity	NPC165711
0.7204	Intermediate Similarity	NPC310236
0.7204	Intermediate Similarity	NPC41217
0.7191	Intermediate Similarity	NPC260956
0.7191	Intermediate Similarity	NPC469799
0.7191	Intermediate Similarity	NPC469806
0.7191	Intermediate Similarity	NPC133391
0.7188	Intermediate Similarity	NPC469995
0.7188	Intermediate Similarity	NPC173875
0.7188	Intermediate Similarity	NPC318282
0.7188	Intermediate Similarity	NPC174948
0.7188	Intermediate Similarity	NPC37646
0.7179	Intermediate Similarity	NPC475795
0.7179	Intermediate Similarity	NPC97322
0.7176	Intermediate Similarity	NPC89374
0.7174	Intermediate Similarity	NPC128644
0.7172	Intermediate Similarity	NPC472924
0.7172	Intermediate Similarity	NPC476223
0.7172	Intermediate Similarity	NPC224720
0.7172	Intermediate Similarity	NPC476240
0.7172	Intermediate Similarity	NPC475099
0.7172	Intermediate Similarity	NPC206079
0.7159	Intermediate Similarity	NPC233352
0.7159	Intermediate Similarity	NPC138492
0.7159	Intermediate Similarity	NPC26139
0.7159	Intermediate Similarity	NPC271104

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 NPC65350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2125
0.2-0.3	4147
0.3-0.4	1884
0.4-0.5	455
0.5-0.6	250
0.6-0.7	92
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7529	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5363	Approved
0.7128	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD4790	Discontinued
0.701	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD5332	Approved
0.6923	Remote Similarity	NPD5331	Approved
0.6882	Remote Similarity	NPD5690	Phase 2
0.6882	Remote Similarity	NPD4519	Discontinued
0.6882	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6848	Remote Similarity	NPD4197	Approved
0.6813	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.68	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD5329	Approved
0.6737	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6703	Remote Similarity	NPD857	Phase 3
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD4694	Approved
0.6701	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.663	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7331	Phase 2
0.6598	Remote Similarity	NPD5207	Approved
0.6596	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD4695	Discontinued
0.6593	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD5208	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6562	Remote Similarity	NPD4518	Approved
0.6559	Remote Similarity	NPD7154	Phase 3
0.6556	Remote Similarity	NPD3617	Approved
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD5693	Phase 1
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD3574	Clinical (unspecified phase)
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
0.6526	Remote Similarity	NPD3618	Phase 1
0.6506	Remote Similarity	NPD7341	Phase 2
0.6495	Remote Similarity	NPD6904	Approved
0.6495	Remote Similarity	NPD4753	Phase 2
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6489	Remote Similarity	NPD4786	Approved
0.6484	Remote Similarity	NPD4195	Approved
0.6465	Remote Similarity	NPD6399	Phase 3
0.6452	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6435	Approved
0.6452	Remote Similarity	NPD3667	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD5211	Phase 2
0.6436	Remote Similarity	NPD7614	Phase 1
0.6436	Remote Similarity	NPD5221	Approved
0.6436	Remote Similarity	NPD5222	Approved
0.6436	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4096	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6421	Remote Similarity	NPD1696	Phase 3
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4821	Approved
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.64	Remote Similarity	NPD6001	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD4271	Approved
0.6373	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6355	Remote Similarity	NPD5697	Approved
0.6354	Remote Similarity	NPD6098	Approved
0.6344	Remote Similarity	NPD5369	Approved
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6371	Approved
0.6327	Remote Similarity	NPD1695	Approved
0.6322	Remote Similarity	NPD4691	Approved
0.6322	Remote Similarity	NPD4747	Approved
0.6321	Remote Similarity	NPD5141	Approved
0.63	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6289	Remote Similarity	NPD3573	Approved
0.6286	Remote Similarity	NPD5091	Approved
0.6277	Remote Similarity	NPD5209	Approved
0.6275	Remote Similarity	NPD4697	Phase 3
0.6264	Remote Similarity	NPD4756	Discovery
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD7639	Approved
0.625	Remote Similarity	NPD5276	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7640	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4755	Approved
0.6211	Remote Similarity	NPD4788	Approved
0.6207	Remote Similarity	NPD4137	Phase 3
0.6204	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD5223	Approved
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.617	Remote Similarity	NPD4139	Approved
0.617	Remote Similarity	NPD4692	Approved
0.6162	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7638	Approved
0.614	Remote Similarity	NPD7115	Discovery
0.6139	Remote Similarity	NPD5133	Approved
0.6132	Remote Similarity	NPD5224	Approved
0.6132	Remote Similarity	NPD5226	Approved
0.6132	Remote Similarity	NPD4633	Approved
0.6132	Remote Similarity	NPD5225	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD4058	Approved
0.6111	Remote Similarity	NPD4687	Approved
0.6111	Remote Similarity	NPD5733	Approved
0.6095	Remote Similarity	NPD4700	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6082	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7748	Approved
0.6078	Remote Similarity	NPD5282	Discontinued
0.6075	Remote Similarity	NPD5175	Approved
0.6075	Remote Similarity	NPD5174	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6071	Remote Similarity	NPD6882	Approved
0.6067	Remote Similarity	NPD6081	Approved
0.6055	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6614	Approved
0.604	Remote Similarity	NPD7637	Suspended
0.602	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD5654	Approved
0.6018	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5979	Remote Similarity	NPD3668	Phase 3
0.5963	Remote Similarity	NPD6008	Approved
0.5962	Remote Similarity	NPD7732	Phase 3
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.5952	Remote Similarity	NPD4194	Approved
0.5952	Remote Similarity	NPD4193	Approved
0.5952	Remote Similarity	NPD4191	Approved
0.5952	Remote Similarity	NPD4192	Approved
0.5949	Remote Similarity	NPD3172	Approved
0.5926	Remote Similarity	NPD6052	Approved
0.5926	Remote Similarity	NPD4754	Approved
0.5913	Remote Similarity	NPD6868	Approved
0.5913	Remote Similarity	NPD6274	Approved
0.5905	Remote Similarity	NPD5959	Approved
0.5905	Remote Similarity	NPD7902	Approved
0.5882	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6411	Approved
0.5875	Remote Similarity	NPD9298	Approved
0.5875	Remote Similarity	NPD3195	Phase 2
0.5875	Remote Similarity	NPD4266	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