NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	1.746
LogD:	1.418
LogS:	-2.648
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	5.314
Fsp3:	0.8
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:	-5.006
MDCK Permeability:	1.707537921902258e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.919
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	66.74256896972656%
Volume Distribution (VD):	0.285
Pgp-substrate:	35.398597717285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.775
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	5.456
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.901
Carcinogencity:	0.862
Eye Corrosion:	0.693
Eye Irritation:	0.924
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC232747

Natural Product ID:	NPC232747
*Common Name:**	2Beta-Hydroxysubergorgic Acid
IUPAC Name:	(1S,3S,3aR,5aR,8S,8aR)-1-hydroxy-3,5a,8-trimethyl-2,3,3a,4,5,8-hexahydro-1H-cyclopenta[h]pentalene-7-carboxylic acid
Synonyms:	2Beta-Hydroxysubergorgic Acid
Standard InCHIKey:	GRJIJCAVEARKHZ-PTHUINEESA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8-6-12(16)15-9(2)10(13(17)18)7-14(15,3)5-4-11(8)15/h7-9,11-12,16H,4-6H2,1-3H3,(H,17,18)/t8-,9+,11+,12-,14+,15+/m0/s1
SMILES:	C[C@H]1C[C@@H]([C@]23[C@@H]1CC[C@]3(C)C=C([C@H]2C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509127
PubChem CID:	11973251
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
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]
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]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456089]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456089]

☑ 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 NPC232747 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	198
0.1-0.2	1294
0.2-0.3	6047
0.3-0.4	15051
0.4-0.5	9211
0.5-0.6	6942
0.6-0.7	3438
0.7-0.8	496
0.8-0.85	15
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC90453
0.8667	High Similarity	NPC290651
0.8605	High Similarity	NPC65350
0.8276	Intermediate Similarity	NPC133844
0.8242	Intermediate Similarity	NPC477215
0.8242	Intermediate Similarity	NPC476388
0.8085	Intermediate Similarity	NPC298919
0.8043	Intermediate Similarity	NPC170775
0.8	Intermediate Similarity	NPC469646
0.8	Intermediate Similarity	NPC476628
0.7938	Intermediate Similarity	NPC197386
0.7935	Intermediate Similarity	NPC477710
0.7931	Intermediate Similarity	NPC261125
0.7931	Intermediate Similarity	NPC181195
0.7907	Intermediate Similarity	NPC276769
0.7889	Intermediate Similarity	NPC238197
0.7889	Intermediate Similarity	NPC7927
0.7889	Intermediate Similarity	NPC230527
0.7882	Intermediate Similarity	NPC474011
0.7872	Intermediate Similarity	NPC221282
0.7849	Intermediate Similarity	NPC97032
0.7835	Intermediate Similarity	NPC477949
0.7831	Intermediate Similarity	NPC254845
0.7812	Intermediate Similarity	NPC37408
0.7789	Intermediate Similarity	NPC37816
0.7778	Intermediate Similarity	NPC472924
0.7778	Intermediate Similarity	NPC475099
0.7766	Intermediate Similarity	NPC37607
0.7766	Intermediate Similarity	NPC301969
0.7766	Intermediate Similarity	NPC477711
0.77	Intermediate Similarity	NPC118405
0.7692	Intermediate Similarity	NPC472958
0.7692	Intermediate Similarity	NPC472957
0.766	Intermediate Similarity	NPC295312
0.766	Intermediate Similarity	NPC123912
0.7634	Intermediate Similarity	NPC237540
0.7629	Intermediate Similarity	NPC469873
0.7629	Intermediate Similarity	NPC472469
0.7629	Intermediate Similarity	NPC52044
0.7614	Intermediate Similarity	NPC192006
0.7609	Intermediate Similarity	NPC245434
0.7604	Intermediate Similarity	NPC125180
0.76	Intermediate Similarity	NPC477950
0.76	Intermediate Similarity	NPC171759
0.7596	Intermediate Similarity	NPC475941
0.7596	Intermediate Similarity	NPC474901
0.7579	Intermediate Similarity	NPC71533
0.7579	Intermediate Similarity	NPC106510
0.7576	Intermediate Similarity	NPC471610
0.7576	Intermediate Similarity	NPC166745
0.7576	Intermediate Similarity	NPC235464
0.7576	Intermediate Similarity	NPC222011
0.757	Intermediate Similarity	NPC471380
0.7553	Intermediate Similarity	NPC249889
0.7553	Intermediate Similarity	NPC474854
0.7553	Intermediate Similarity	NPC193843
0.7553	Intermediate Similarity	NPC91248
0.7551	Intermediate Similarity	NPC18019
0.7551	Intermediate Similarity	NPC24956
0.7527	Intermediate Similarity	NPC56593
0.7526	Intermediate Similarity	NPC323008
0.7526	Intermediate Similarity	NPC262133
0.7526	Intermediate Similarity	NPC470013
0.7526	Intermediate Similarity	NPC470010
0.7525	Intermediate Similarity	NPC195290
0.7525	Intermediate Similarity	NPC204450
0.7524	Intermediate Similarity	NPC179642
0.75	Intermediate Similarity	NPC287833
0.75	Intermediate Similarity	NPC306856
0.75	Intermediate Similarity	NPC218383
0.75	Intermediate Similarity	NPC165064
0.75	Intermediate Similarity	NPC472326
0.75	Intermediate Similarity	NPC476274
0.75	Intermediate Similarity	NPC86917
0.75	Intermediate Similarity	NPC470074
0.75	Intermediate Similarity	NPC471041
0.7476	Intermediate Similarity	NPC243998
0.7475	Intermediate Similarity	NPC69385
0.7475	Intermediate Similarity	NPC161493
0.7474	Intermediate Similarity	NPC41217
0.7474	Intermediate Similarity	NPC268298
0.7474	Intermediate Similarity	NPC214387
0.7474	Intermediate Similarity	NPC310236
0.7473	Intermediate Similarity	NPC256750
0.7473	Intermediate Similarity	NPC20262
0.747	Intermediate Similarity	NPC477791
0.7451	Intermediate Similarity	NPC236390
0.7449	Intermediate Similarity	NPC469995
0.7449	Intermediate Similarity	NPC174948
0.7449	Intermediate Similarity	NPC476487
0.7449	Intermediate Similarity	NPC173875
0.7449	Intermediate Similarity	NPC318282
0.7449	Intermediate Similarity	NPC67584
0.7449	Intermediate Similarity	NPC472932
0.7449	Intermediate Similarity	NPC476174
0.7449	Intermediate Similarity	NPC476488
0.7449	Intermediate Similarity	NPC170120
0.7447	Intermediate Similarity	NPC471657
0.7447	Intermediate Similarity	NPC45957
0.7444	Intermediate Similarity	NPC271104
0.7444	Intermediate Similarity	NPC476625
0.7444	Intermediate Similarity	NPC45495
0.7442	Intermediate Similarity	NPC14352
0.7442	Intermediate Similarity	NPC234527
0.7426	Intermediate Similarity	NPC150923
0.7426	Intermediate Similarity	NPC304738
0.7426	Intermediate Similarity	NPC116139
0.7426	Intermediate Similarity	NPC476223
0.7426	Intermediate Similarity	NPC476240
0.7426	Intermediate Similarity	NPC195192
0.7426	Intermediate Similarity	NPC224720
0.7423	Intermediate Similarity	NPC200237
0.7423	Intermediate Similarity	NPC206810
0.7423	Intermediate Similarity	NPC135776
0.7423	Intermediate Similarity	NPC109414
0.7419	Intermediate Similarity	NPC137033
0.7419	Intermediate Similarity	NPC179006
0.7419	Intermediate Similarity	NPC36350
0.7419	Intermediate Similarity	NPC474853
0.7416	Intermediate Similarity	NPC169095
0.7416	Intermediate Similarity	NPC172066
0.7404	Intermediate Similarity	NPC472925
0.74	Intermediate Similarity	NPC114274
0.74	Intermediate Similarity	NPC221615
0.74	Intermediate Similarity	NPC244411
0.74	Intermediate Similarity	NPC141191
0.74	Intermediate Similarity	NPC23364
0.74	Intermediate Similarity	NPC471717
0.7396	Intermediate Similarity	NPC477147
0.7396	Intermediate Similarity	NPC2946
0.7396	Intermediate Similarity	NPC477149
0.7396	Intermediate Similarity	NPC472466
0.7396	Intermediate Similarity	NPC77337
0.7396	Intermediate Similarity	NPC129419
0.7391	Intermediate Similarity	NPC477667
0.7391	Intermediate Similarity	NPC472473
0.7391	Intermediate Similarity	NPC474748
0.7386	Intermediate Similarity	NPC215481
0.7386	Intermediate Similarity	NPC279537
0.7383	Intermediate Similarity	NPC475970
0.7379	Intermediate Similarity	NPC309190
0.7374	Intermediate Similarity	NPC213078
0.7374	Intermediate Similarity	NPC173272
0.7374	Intermediate Similarity	NPC185553
0.7374	Intermediate Similarity	NPC328371
0.7374	Intermediate Similarity	NPC472941
0.7374	Intermediate Similarity	NPC126156
0.7374	Intermediate Similarity	NPC184065
0.7374	Intermediate Similarity	NPC456
0.7368	Intermediate Similarity	NPC472870
0.7364	Intermediate Similarity	NPC161060
0.7363	Intermediate Similarity	NPC88735
0.7363	Intermediate Similarity	NPC47031
0.7363	Intermediate Similarity	NPC472471
0.7353	Intermediate Similarity	NPC293753
0.7353	Intermediate Similarity	NPC66110
0.7353	Intermediate Similarity	NPC86077
0.7349	Intermediate Similarity	NPC162309
0.7347	Intermediate Similarity	NPC53685
0.7347	Intermediate Similarity	NPC198853
0.7347	Intermediate Similarity	NPC477131
0.734	Intermediate Similarity	NPC232156
0.734	Intermediate Similarity	NPC67493
0.734	Intermediate Similarity	NPC472869
0.734	Intermediate Similarity	NPC477668
0.7333	Intermediate Similarity	NPC476624
0.7333	Intermediate Similarity	NPC471890
0.7333	Intermediate Similarity	NPC7232
0.7333	Intermediate Similarity	NPC66677
0.7333	Intermediate Similarity	NPC472013
0.7333	Intermediate Similarity	NPC84185
0.7333	Intermediate Similarity	NPC469690
0.7327	Intermediate Similarity	NPC241221
0.7327	Intermediate Similarity	NPC51370
0.7327	Intermediate Similarity	NPC280963
0.7326	Intermediate Similarity	NPC29328
0.732	Intermediate Similarity	NPC131209
0.732	Intermediate Similarity	NPC45269
0.732	Intermediate Similarity	NPC261607
0.732	Intermediate Similarity	NPC300312
0.732	Intermediate Similarity	NPC475925
0.732	Intermediate Similarity	NPC472468
0.732	Intermediate Similarity	NPC111114
0.7315	Intermediate Similarity	NPC312017
0.7315	Intermediate Similarity	NPC9848
0.7312	Intermediate Similarity	NPC164577
0.7312	Intermediate Similarity	NPC19849
0.7312	Intermediate Similarity	NPC472865
0.7312	Intermediate Similarity	NPC472864
0.7308	Intermediate Similarity	NPC223450
0.7308	Intermediate Similarity	NPC314244
0.73	Intermediate Similarity	NPC18319
0.73	Intermediate Similarity	NPC213947
0.73	Intermediate Similarity	NPC87090
0.73	Intermediate Similarity	NPC108475
0.73	Intermediate Similarity	NPC169205
0.73	Intermediate Similarity	NPC475894
0.73	Intermediate Similarity	NPC170143
0.73	Intermediate Similarity	NPC320306
0.7292	Intermediate Similarity	NPC155935

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 NPC232747 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	1998
0.2-0.3	4086
0.3-0.4	2032
0.4-0.5	449
0.5-0.6	226
0.6-0.7	152
0.7-0.8	17
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
0.7978	Intermediate Similarity	NPD5362	Discontinued
0.7753	Intermediate Similarity	NPD4790	Discontinued
0.7614	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5363	Approved
0.7582	Intermediate Similarity	NPD5332	Approved
0.7582	Intermediate Similarity	NPD5331	Approved
0.7579	Intermediate Similarity	NPD5785	Approved
0.734	Intermediate Similarity	NPD5786	Approved
0.7283	Intermediate Similarity	NPD4269	Approved
0.7283	Intermediate Similarity	NPD4270	Approved
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5368	Approved
0.7128	Intermediate Similarity	NPD3133	Approved
0.7128	Intermediate Similarity	NPD3666	Approved
0.7128	Intermediate Similarity	NPD3665	Phase 1
0.7097	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD4252	Approved
0.7065	Intermediate Similarity	NPD4822	Approved
0.7065	Intermediate Similarity	NPD4821	Approved
0.7065	Intermediate Similarity	NPD4820	Approved
0.7065	Intermediate Similarity	NPD4819	Approved
0.7064	Intermediate Similarity	NPD6053	Discontinued
0.7053	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD4271	Approved
0.7033	Intermediate Similarity	NPD4268	Approved
0.7021	Intermediate Similarity	NPD7154	Phase 3
0.7019	Intermediate Similarity	NPD5211	Phase 2
0.701	Intermediate Similarity	NPD6903	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD7639	Approved
0.699	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD4249	Approved
0.697	Remote Similarity	NPD6079	Approved
0.6939	Remote Similarity	NPD5328	Approved
0.6939	Remote Similarity	NPD1695	Approved
0.6916	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD4250	Approved
0.6907	Remote Similarity	NPD4251	Approved
0.6893	Remote Similarity	NPD7638	Approved
0.6887	Remote Similarity	NPD5141	Approved
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6011	Approved
0.6852	Remote Similarity	NPD6881	Approved
0.6852	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD4696	Approved
0.6827	Remote Similarity	NPD5286	Approved
0.6827	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6809	Remote Similarity	NPD5369	Approved
0.6804	Remote Similarity	NPD7146	Approved
0.6804	Remote Similarity	NPD6409	Approved
0.6804	Remote Similarity	NPD7334	Approved
0.6804	Remote Similarity	NPD5330	Approved
0.6804	Remote Similarity	NPD7521	Approved
0.6804	Remote Similarity	NPD6684	Approved
0.6804	Remote Similarity	NPD5279	Phase 3
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD4755	Approved
0.6796	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6768	Remote Similarity	NPD4753	Phase 2
0.6765	Remote Similarity	NPD5695	Phase 3
0.6762	Remote Similarity	NPD5223	Approved
0.6759	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5701	Approved
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD4202	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6727	Remote Similarity	NPD7290	Approved
0.6727	Remote Similarity	NPD6883	Approved
0.6727	Remote Similarity	NPD7102	Approved
0.6699	Remote Similarity	NPD5221	Approved
0.6699	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5222	Approved
0.6698	Remote Similarity	NPD5225	Approved
0.6698	Remote Similarity	NPD5226	Approved
0.6698	Remote Similarity	NPD4633	Approved
0.6698	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD5173	Approved
0.6634	Remote Similarity	NPD5284	Approved
0.6634	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD5281	Approved
0.6633	Remote Similarity	NPD3618	Phase 1
0.6633	Remote Similarity	NPD5690	Phase 2
0.6607	Remote Similarity	NPD8297	Approved
0.6607	Remote Similarity	NPD6882	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD5210	Approved
0.6598	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6583	Remote Similarity	NPD7078	Approved
0.6577	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5696	Approved
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD4697	Phase 3
0.6531	Remote Similarity	NPD5329	Approved
0.6531	Remote Similarity	NPD1694	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7507	Approved
0.6496	Remote Similarity	NPD6319	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD4754	Approved
0.6471	Remote Similarity	NPD7983	Approved
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4138	Approved
0.6465	Remote Similarity	NPD5280	Approved
0.6465	Remote Similarity	NPD4694	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD4689	Approved
0.6465	Remote Similarity	NPD4688	Approved
0.6441	Remote Similarity	NPD5983	Phase 2
0.6435	Remote Similarity	NPD6274	Approved
0.6421	Remote Similarity	NPD6929	Approved
0.6417	Remote Similarity	NPD7492	Approved
0.6408	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6686	Approved
0.6396	Remote Similarity	NPD4729	Approved
0.6396	Remote Similarity	NPD5128	Approved
0.6396	Remote Similarity	NPD4730	Approved
0.6392	Remote Similarity	NPD5209	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6379	Remote Similarity	NPD6317	Approved
0.6373	Remote Similarity	NPD5207	Approved
0.6373	Remote Similarity	NPD46	Approved
0.6373	Remote Similarity	NPD6698	Approved
0.6364	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD1696	Phase 3
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4767	Approved
0.6356	Remote Similarity	NPD6054	Approved
0.6355	Remote Similarity	NPD6404	Discontinued
0.6354	Remote Similarity	NPD6931	Approved
0.6354	Remote Similarity	NPD6930	Phase 2
0.6346	Remote Similarity	NPD5282	Discontinued
0.6341	Remote Similarity	NPD7319	Approved
0.6337	Remote Similarity	NPD4518	Approved
0.6337	Remote Similarity	NPD5208	Approved
0.6337	Remote Similarity	NPD6672	Approved
0.6337	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD7604	Phase 2
0.6325	Remote Similarity	NPD6313	Approved
0.6325	Remote Similarity	NPD6314	Approved
0.6325	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD5693	Phase 1
0.6306	Remote Similarity	NPD6412	Phase 2
0.6303	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6016	Approved
0.6303	Remote Similarity	NPD6015	Approved
0.63	Remote Similarity	NPD4519	Discontinued
0.63	Remote Similarity	NPD4623	Approved
0.6289	Remote Similarity	NPD857	Phase 3
0.6286	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5135	Approved
0.6283	Remote Similarity	NPD5251	Approved
0.6283	Remote Similarity	NPD5247	Approved
0.6283	Remote Similarity	NPD5249	Phase 3
0.6283	Remote Similarity	NPD5250	Approved
0.6283	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5169	Approved
0.6283	Remote Similarity	NPD5248	Approved
0.6275	Remote Similarity	NPD6673	Approved
0.6275	Remote Similarity	NPD6080	Approved
0.6275	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD7100	Approved
0.6271	Remote Similarity	NPD7101	Approved
0.6262	Remote Similarity	NPD4225	Approved
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD6370	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