NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	320.2
Volume:	338.762
LogP:	2.16
LogD:	1.72
LogS:	-2.354
# Rotatable Bonds:	2
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	4.494
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.636
MDCK Permeability:	1.1934143913094886e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	53.012550354003906%
Volume Distribution (VD):	0.554
Pgp-substrate:	49.848060607910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.787
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.524
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	5.82
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.381
Skin Sensitization:	0.266
Carcinogencity:	0.421
Eye Corrosion:	0.883
Eye Irritation:	0.124
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC476810

Natural Product ID:	NPC476810
*Common Name:**	Tagalsin R
IUPAC Name:	(2S,4aS,4bR,8Z,8aS,10aS)-8-(hydroxymethylidene)-2,4a,8a-trimethyl-7-oxo-3,4,4b,5,6,9,10,10a-octahydro-1H-phenanthrene-2-carboxylic acid
Synonyms:	Tagalsin R
Standard InCHIKey:	AJXRWZCVCLQXAV-IBDIHCAMSA-N
Standard InCHI:	InChI=1S/C19H28O4/c1-17(16(22)23)8-9-18(2)12(10-17)6-7-19(3)13(11-20)14(21)4-5-15(18)19/h11-12,15,20H,4-10H2,1-3H3,(H,22,23)/b13-11+/t12-,15+,17-,18-,19+/m0/s1
SMILES:	C[C@@]1(CC[C@]2([C@H](C1)CC[C@]\3([C@@H]2CCC(=O)/C3=C\O)C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49831501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids [CHEMONTID:0003368] 3-carboxy steroids

*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
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378377]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	the mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	40	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	37	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	18	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	28	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	30	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	7	%	PMID[20886837]

☑ 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 NPC476810 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	193
0.1-0.2	1606
0.2-0.3	6440
0.3-0.4	15357
0.4-0.5	7304
0.5-0.6	6234
0.6-0.7	4065
0.7-0.8	1394
0.8-0.85	95
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC476811
0.9079	High Similarity	NPC476812
0.8816	High Similarity	NPC106078
0.8816	High Similarity	NPC471035
0.8816	High Similarity	NPC149249
0.8816	High Similarity	NPC212661
0.8514	High Similarity	NPC91369
0.8452	Intermediate Similarity	NPC477973
0.8415	Intermediate Similarity	NPC474680
0.8415	Intermediate Similarity	NPC201655
0.8395	Intermediate Similarity	NPC105803
0.8375	Intermediate Similarity	NPC278459
0.8375	Intermediate Similarity	NPC90055
0.8354	Intermediate Similarity	NPC471475
0.8354	Intermediate Similarity	NPC192329
0.8333	Intermediate Similarity	NPC56413
0.8333	Intermediate Similarity	NPC474433
0.8313	Intermediate Similarity	NPC70661
0.8289	Intermediate Similarity	NPC330659
0.8289	Intermediate Similarity	NPC244708
0.8289	Intermediate Similarity	NPC161187
0.8289	Intermediate Similarity	NPC472813
0.8289	Intermediate Similarity	NPC36310
0.8272	Intermediate Similarity	NPC170985
0.8267	Intermediate Similarity	NPC235586
0.8256	Intermediate Similarity	NPC211403
0.8256	Intermediate Similarity	NPC198242
0.8256	Intermediate Similarity	NPC250753
0.8243	Intermediate Similarity	NPC290445
0.8243	Intermediate Similarity	NPC36616
0.8214	Intermediate Similarity	NPC173089
0.8214	Intermediate Similarity	NPC158141
0.8205	Intermediate Similarity	NPC246445
0.8171	Intermediate Similarity	NPC243347
0.8171	Intermediate Similarity	NPC118800
0.8171	Intermediate Similarity	NPC291320
0.8171	Intermediate Similarity	NPC471036
0.8171	Intermediate Similarity	NPC472740
0.8171	Intermediate Similarity	NPC245866
0.8171	Intermediate Similarity	NPC471037
0.8171	Intermediate Similarity	NPC175410
0.8161	Intermediate Similarity	NPC294263
0.8158	Intermediate Similarity	NPC72343
0.8148	Intermediate Similarity	NPC471898
0.8125	Intermediate Similarity	NPC192744
0.8125	Intermediate Similarity	NPC201459
0.8125	Intermediate Similarity	NPC263951
0.8118	Intermediate Similarity	NPC474511
0.8118	Intermediate Similarity	NPC474719
0.8118	Intermediate Similarity	NPC1753
0.8101	Intermediate Similarity	NPC165711
0.8101	Intermediate Similarity	NPC66105
0.8101	Intermediate Similarity	NPC472746
0.8095	Intermediate Similarity	NPC56588
0.8095	Intermediate Similarity	NPC80590
0.8095	Intermediate Similarity	NPC34190
0.8095	Intermediate Similarity	NPC322159
0.8095	Intermediate Similarity	NPC185638
0.8095	Intermediate Similarity	NPC2783
0.8095	Intermediate Similarity	NPC187545
0.8095	Intermediate Similarity	NPC324063
0.8077	Intermediate Similarity	NPC39362
0.8072	Intermediate Similarity	NPC96095
0.8072	Intermediate Similarity	NPC130966
0.8072	Intermediate Similarity	NPC146683
0.8072	Intermediate Similarity	NPC263974
0.8068	Intermediate Similarity	NPC272635
0.8068	Intermediate Similarity	NPC47853
0.8068	Intermediate Similarity	NPC470385
0.8068	Intermediate Similarity	NPC470386
0.8068	Intermediate Similarity	NPC169751
0.8052	Intermediate Similarity	NPC177826
0.8049	Intermediate Similarity	NPC476292
0.8049	Intermediate Similarity	NPC474605
0.8049	Intermediate Similarity	NPC103486
0.8046	Intermediate Similarity	NPC230064
0.8046	Intermediate Similarity	NPC233455
0.8046	Intermediate Similarity	NPC158030
0.8046	Intermediate Similarity	NPC145067
0.8046	Intermediate Similarity	NPC4036
0.8046	Intermediate Similarity	NPC65120
0.8025	Intermediate Similarity	NPC477057
0.8025	Intermediate Similarity	NPC104545
0.8025	Intermediate Similarity	NPC37038
0.8025	Intermediate Similarity	NPC2482
0.8025	Intermediate Similarity	NPC472478
0.8023	Intermediate Similarity	NPC281524
0.8	Intermediate Similarity	NPC260385
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC269543
0.8	Intermediate Similarity	NPC153604
0.8	Intermediate Similarity	NPC259009
0.8	Intermediate Similarity	NPC134197
0.8	Intermediate Similarity	NPC269360
0.8	Intermediate Similarity	NPC280654
0.8	Intermediate Similarity	NPC96496
0.8	Intermediate Similarity	NPC174619
0.8	Intermediate Similarity	NPC33768
0.8	Intermediate Similarity	NPC264005
0.8	Intermediate Similarity	NPC110094
0.8	Intermediate Similarity	NPC247783
0.7978	Intermediate Similarity	NPC139459
0.7978	Intermediate Similarity	NPC470232
0.7978	Intermediate Similarity	NPC476174
0.7978	Intermediate Similarity	NPC210214
0.7978	Intermediate Similarity	NPC98639
0.7976	Intermediate Similarity	NPC264317
0.7976	Intermediate Similarity	NPC76518
0.7976	Intermediate Similarity	NPC102292
0.7976	Intermediate Similarity	NPC190704
0.7976	Intermediate Similarity	NPC474537
0.7976	Intermediate Similarity	NPC294438
0.7976	Intermediate Similarity	NPC471034
0.7975	Intermediate Similarity	NPC180886
0.7975	Intermediate Similarity	NPC104806
0.7975	Intermediate Similarity	NPC20466
0.7975	Intermediate Similarity	NPC476601
0.7975	Intermediate Similarity	NPC89294
0.7973	Intermediate Similarity	NPC103734
0.7955	Intermediate Similarity	NPC214756
0.7955	Intermediate Similarity	NPC272075
0.7955	Intermediate Similarity	NPC295643
0.7952	Intermediate Similarity	NPC215893
0.7949	Intermediate Similarity	NPC255168
0.7931	Intermediate Similarity	NPC46441
0.7931	Intermediate Similarity	NPC291028
0.7931	Intermediate Similarity	NPC252737
0.7931	Intermediate Similarity	NPC193750
0.7927	Intermediate Similarity	NPC103754
0.7927	Intermediate Similarity	NPC263272
0.7927	Intermediate Similarity	NPC3915
0.7927	Intermediate Similarity	NPC274050
0.7927	Intermediate Similarity	NPC328264
0.7927	Intermediate Similarity	NPC116797
0.7927	Intermediate Similarity	NPC267691
0.7927	Intermediate Similarity	NPC121984
0.7927	Intermediate Similarity	NPC162632
0.7927	Intermediate Similarity	NPC474484
0.7907	Intermediate Similarity	NPC182797
0.7907	Intermediate Similarity	NPC16377
0.7907	Intermediate Similarity	NPC52169
0.7907	Intermediate Similarity	NPC211162
0.7907	Intermediate Similarity	NPC474474
0.7907	Intermediate Similarity	NPC183374
0.7901	Intermediate Similarity	NPC231431
0.7901	Intermediate Similarity	NPC199595
0.7901	Intermediate Similarity	NPC472490
0.7901	Intermediate Similarity	NPC474113
0.7889	Intermediate Similarity	NPC13949
0.7889	Intermediate Similarity	NPC200054
0.7889	Intermediate Similarity	NPC470387
0.7889	Intermediate Similarity	NPC104568
0.7889	Intermediate Similarity	NPC219353
0.7889	Intermediate Similarity	NPC29152
0.7889	Intermediate Similarity	NPC329910
0.7889	Intermediate Similarity	NPC29410
0.7882	Intermediate Similarity	NPC73038
0.7882	Intermediate Similarity	NPC472505
0.7882	Intermediate Similarity	NPC229717
0.7882	Intermediate Similarity	NPC12774
0.7882	Intermediate Similarity	NPC72638
0.7882	Intermediate Similarity	NPC471042
0.7875	Intermediate Similarity	NPC471899
0.7875	Intermediate Similarity	NPC107039
0.7875	Intermediate Similarity	NPC68828
0.7875	Intermediate Similarity	NPC472300
0.7875	Intermediate Similarity	NPC471897
0.7875	Intermediate Similarity	NPC238227
0.7865	Intermediate Similarity	NPC475118
0.7857	Intermediate Similarity	NPC171789
0.7857	Intermediate Similarity	NPC248758
0.7848	Intermediate Similarity	NPC279666
0.7848	Intermediate Similarity	NPC192540
0.7848	Intermediate Similarity	NPC179858
0.7848	Intermediate Similarity	NPC201027
0.7848	Intermediate Similarity	NPC472311
0.7841	Intermediate Similarity	NPC6255
0.7841	Intermediate Similarity	NPC105189
0.7841	Intermediate Similarity	NPC471588
0.7841	Intermediate Similarity	NPC198054
0.7841	Intermediate Similarity	NPC174167
0.7841	Intermediate Similarity	NPC470036
0.7841	Intermediate Similarity	NPC474525
0.7841	Intermediate Similarity	NPC38754
0.7831	Intermediate Similarity	NPC46881
0.7831	Intermediate Similarity	NPC73882
0.7831	Intermediate Similarity	NPC145143
0.7831	Intermediate Similarity	NPC69101
0.7831	Intermediate Similarity	NPC238991
0.7831	Intermediate Similarity	NPC110780
0.7831	Intermediate Similarity	NPC310989
0.7831	Intermediate Similarity	NPC251779
0.7831	Intermediate Similarity	NPC302661
0.7831	Intermediate Similarity	NPC477858
0.7821	Intermediate Similarity	NPC279241
0.7816	Intermediate Similarity	NPC5509
0.7816	Intermediate Similarity	NPC57954
0.7816	Intermediate Similarity	NPC24772
0.7816	Intermediate Similarity	NPC234346

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 NPC476810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2109
0.2-0.3	3928
0.3-0.4	1994
0.4-0.5	509
0.5-0.6	210
0.6-0.7	157
0.7-0.8	53
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8395	Intermediate Similarity	NPD4788	Approved
0.8046	Intermediate Similarity	NPD7515	Phase 2
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4695	Discontinued
0.7733	Intermediate Similarity	NPD4224	Phase 2
0.7667	Intermediate Similarity	NPD7748	Approved
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7647	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD3667	Approved
0.7561	Intermediate Similarity	NPD3617	Approved
0.7531	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3618	Phase 1
0.7468	Intermediate Similarity	NPD6081	Approved
0.7444	Intermediate Similarity	NPD8035	Phase 2
0.7444	Intermediate Similarity	NPD8034	Phase 2
0.7442	Intermediate Similarity	NPD4786	Approved
0.7439	Intermediate Similarity	NPD6116	Phase 1
0.7436	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3698	Phase 2
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD7902	Approved
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6399	Phase 3
0.7349	Intermediate Similarity	NPD6114	Approved
0.7349	Intermediate Similarity	NPD6697	Approved
0.7349	Intermediate Similarity	NPD6115	Approved
0.7349	Intermediate Similarity	NPD6118	Approved
0.7342	Intermediate Similarity	NPD4245	Approved
0.7342	Intermediate Similarity	NPD4789	Approved
0.7342	Intermediate Similarity	NPD4244	Approved
0.7312	Intermediate Similarity	NPD7614	Phase 1
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7146	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5328	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7204	Intermediate Similarity	NPD4629	Approved
0.7204	Intermediate Similarity	NPD5210	Approved
0.7204	Intermediate Similarity	NPD5695	Phase 3
0.7158	Intermediate Similarity	NPD5696	Approved
0.7128	Intermediate Similarity	NPD5221	Approved
0.7128	Intermediate Similarity	NPD5222	Approved
0.7128	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6903	Approved
0.7097	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7900	Approved
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7065	Intermediate Similarity	NPD5284	Approved
0.7065	Intermediate Similarity	NPD5281	Approved
0.7053	Intermediate Similarity	NPD5173	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7045	Intermediate Similarity	NPD4197	Approved
0.7037	Intermediate Similarity	NPD5777	Approved
0.7	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD5697	Approved
0.6989	Remote Similarity	NPD4202	Approved
0.6988	Remote Similarity	NPD3703	Phase 2
0.6988	Remote Similarity	NPD3702	Approved
0.6979	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD5329	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD7732	Phase 3
0.6931	Remote Similarity	NPD6011	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6907	Remote Similarity	NPD4696	Approved
0.6907	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD5286	Approved
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD4519	Discontinued
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD4623	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6889	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD5360	Phase 3
0.6875	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD6012	Approved
0.6863	Remote Similarity	NPD6014	Approved
0.6848	Remote Similarity	NPD6673	Approved
0.6848	Remote Similarity	NPD6904	Approved
0.6848	Remote Similarity	NPD6080	Approved
0.6837	Remote Similarity	NPD5223	Approved
0.6832	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6768	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5224	Approved
0.6768	Remote Similarity	NPD5225	Approved
0.6768	Remote Similarity	NPD5226	Approved
0.6768	Remote Similarity	NPD4633	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6744	Remote Similarity	NPD3671	Phase 1
0.6739	Remote Similarity	NPD5208	Approved
0.6735	Remote Similarity	NPD4700	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6707	Remote Similarity	NPD4691	Approved
0.6705	Remote Similarity	NPD4139	Approved
0.6705	Remote Similarity	NPD4692	Approved
0.6703	Remote Similarity	NPD6098	Approved
0.6703	Remote Similarity	NPD5280	Approved
0.6703	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD5693	Phase 1
0.67	Remote Similarity	NPD5174	Approved
0.67	Remote Similarity	NPD5175	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6627	Remote Similarity	NPD4758	Discontinued
0.6604	Remote Similarity	NPD4632	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.6596	Remote Similarity	NPD5692	Phase 3
0.6593	Remote Similarity	NPD1694	Approved
0.6591	Remote Similarity	NPD7525	Registered
0.6585	Remote Similarity	NPD4137	Phase 3
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4754	Approved
0.6526	Remote Similarity	NPD6050	Approved
0.6526	Remote Similarity	NPD5694	Approved
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4747	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6274	Approved
0.6481	Remote Similarity	NPD6868	Approved
0.6477	Remote Similarity	NPD7645	Phase 2
0.6471	Remote Similarity	NPD4058	Approved
0.6465	Remote Similarity	NPD4225	Approved
0.6442	Remote Similarity	NPD5168	Approved
0.6442	Remote Similarity	NPD4730	Approved
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4729	Approved
0.6442	Remote Similarity	NPD5128	Approved
0.6422	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD6317	Approved
0.6422	Remote Similarity	NPD6009	Approved
0.6421	Remote Similarity	NPD5207	Approved
0.6408	Remote Similarity	NPD4767	Approved
0.6408	Remote Similarity	NPD4768	Approved
0.6395	Remote Similarity	NPD7339	Approved
0.6395	Remote Similarity	NPD6942	Approved
0.6392	Remote Similarity	NPD6001	Approved
0.6381	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD5364	Discontinued
0.6364	Remote Similarity	NPD6313	Approved
0.6364	Remote Similarity	NPD6314	Approved
0.6327	Remote Similarity	NPD5654	Approved
0.6321	Remote Similarity	NPD5135	Approved
0.6321	Remote Similarity	NPD5248	Approved
0.6321	Remote Similarity	NPD5250	Approved
0.6321	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5169	Approved
0.6321	Remote Similarity	NPD5251	Approved
0.6321	Remote Similarity	NPD5247	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