NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	292.2
Volume:	315.313
LogP:	2.453
LogD:	2.07
LogS:	-2.3
# Rotatable Bonds:	0
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	4.557
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.644
MDCK Permeability:	3.374446532689035e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.688
Plasma Protein Binding (PPB):	77.12409973144531%
Volume Distribution (VD):	0.394
Pgp-substrate:	30.810937881469727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.838
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	18.601
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.413
Maximum Recommended Daily Dose:	0.831
Skin Sensitization:	0.732
Carcinogencity:	0.89
Eye Corrosion:	0.369
Eye Irritation:	0.097
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC476808

Natural Product ID:	NPC476808
*Common Name:**	Tagalsin P
IUPAC Name:	(4aR,4bS,7S,8aS,10aS)-2,7-dihydroxy-1,4b,7,10a-tetramethyl-4,4a,5,6,8,8a,9,10-octahydrophenanthren-3-one
Synonyms:	Tagalsin P
Standard InCHIKey:	HBRFKORKLCCQOQ-IDOKYYSUSA-N
Standard InCHI:	InChI=1S/C18H28O3/c1-11-15(20)13(19)9-14-17(11,3)6-5-12-10-16(2,21)7-8-18(12,14)4/h12,14,20-21H,5-10H2,1-4H3/t12-,14-,16-,17+,18-/m0/s1
SMILES:	CC1=C(C(=O)C[C@H]2[C@@]1(CC[C@@H]3[C@@]2(CC[C@](C3)(C)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49831499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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	=	48	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	18	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	14	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	22	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	6	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	2	%	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 NPC476808 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	1589
0.2-0.3	6619
0.3-0.4	15586
0.4-0.5	8672
0.5-0.6	5735
0.6-0.7	3375
0.7-0.8	865
0.8-0.85	47
0.85-0.9	13
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC92080
0.9079	High Similarity	NPC192329
0.8961	High Similarity	NPC476809
0.8961	High Similarity	NPC18955
0.8947	High Similarity	NPC30321
0.8718	High Similarity	NPC108955
0.8718	High Similarity	NPC469637
0.8675	High Similarity	NPC65615
0.8675	High Similarity	NPC68148
0.8625	High Similarity	NPC105803
0.8625	High Similarity	NPC53733
0.8608	High Similarity	NPC473217
0.8608	High Similarity	NPC55869
0.8571	High Similarity	NPC474209
0.8571	High Similarity	NPC475823
0.8571	High Similarity	NPC257666
0.8571	High Similarity	NPC266193
0.8519	High Similarity	NPC144258
0.8514	High Similarity	NPC163020
0.8415	Intermediate Similarity	NPC474680
0.8415	Intermediate Similarity	NPC6185
0.8415	Intermediate Similarity	NPC241512
0.8375	Intermediate Similarity	NPC225515
0.8354	Intermediate Similarity	NPC170394
0.8333	Intermediate Similarity	NPC165711
0.8333	Intermediate Similarity	NPC230387
0.8313	Intermediate Similarity	NPC94666
0.8312	Intermediate Similarity	NPC175079
0.8293	Intermediate Similarity	NPC237712
0.8272	Intermediate Similarity	NPC103486
0.8272	Intermediate Similarity	NPC48362
0.8272	Intermediate Similarity	NPC193347
0.8256	Intermediate Similarity	NPC248913
0.825	Intermediate Similarity	NPC2482
0.8228	Intermediate Similarity	NPC471409
0.8228	Intermediate Similarity	NPC275494
0.8228	Intermediate Similarity	NPC189485
0.8214	Intermediate Similarity	NPC471792
0.8205	Intermediate Similarity	NPC76966
0.8205	Intermediate Similarity	NPC186554
0.8205	Intermediate Similarity	NPC472305
0.8193	Intermediate Similarity	NPC8518
0.8193	Intermediate Similarity	NPC263997
0.8193	Intermediate Similarity	NPC132228
0.8193	Intermediate Similarity	NPC469993
0.8182	Intermediate Similarity	NPC470299
0.8148	Intermediate Similarity	NPC121984
0.8148	Intermediate Similarity	NPC471898
0.8148	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC27817
0.8118	Intermediate Similarity	NPC48107
0.8101	Intermediate Similarity	NPC476811
0.8095	Intermediate Similarity	NPC327115
0.8095	Intermediate Similarity	NPC158393
0.8072	Intermediate Similarity	NPC251170
0.8068	Intermediate Similarity	NPC212812
0.8068	Intermediate Similarity	NPC474328
0.8068	Intermediate Similarity	NPC23170
0.8068	Intermediate Similarity	NPC160413
0.8052	Intermediate Similarity	NPC247586
0.8049	Intermediate Similarity	NPC469325
0.8046	Intermediate Similarity	NPC185936
0.8046	Intermediate Similarity	NPC168027
0.8023	Intermediate Similarity	NPC326627
0.8023	Intermediate Similarity	NPC112454
0.8023	Intermediate Similarity	NPC310010
0.8	Intermediate Similarity	NPC220930
0.8	Intermediate Similarity	NPC207772
0.8	Intermediate Similarity	NPC272039
0.7978	Intermediate Similarity	NPC280725
0.7978	Intermediate Similarity	NPC147232
0.7976	Intermediate Similarity	NPC470574
0.7976	Intermediate Similarity	NPC33663
0.7976	Intermediate Similarity	NPC197823
0.7975	Intermediate Similarity	NPC180886
0.7975	Intermediate Similarity	NPC1254
0.7973	Intermediate Similarity	NPC103734
0.7955	Intermediate Similarity	NPC211230
0.7952	Intermediate Similarity	NPC472492
0.7952	Intermediate Similarity	NPC64600
0.7949	Intermediate Similarity	NPC162164
0.7949	Intermediate Similarity	NPC38426
0.7931	Intermediate Similarity	NPC38952
0.7931	Intermediate Similarity	NPC252737
0.7927	Intermediate Similarity	NPC474085
0.7927	Intermediate Similarity	NPC44963
0.7927	Intermediate Similarity	NPC226068
0.7927	Intermediate Similarity	NPC472684
0.7922	Intermediate Similarity	NPC144627
0.7922	Intermediate Similarity	NPC84790
0.7907	Intermediate Similarity	NPC328539
0.7907	Intermediate Similarity	NPC475001
0.7907	Intermediate Similarity	NPC307298
0.7907	Intermediate Similarity	NPC185059
0.7907	Intermediate Similarity	NPC472802
0.7907	Intermediate Similarity	NPC58271
0.7901	Intermediate Similarity	NPC475681
0.7901	Intermediate Similarity	NPC231431
0.7901	Intermediate Similarity	NPC474113
0.7901	Intermediate Similarity	NPC215843
0.7889	Intermediate Similarity	NPC272411
0.7882	Intermediate Similarity	NPC145879
0.7882	Intermediate Similarity	NPC472479
0.7882	Intermediate Similarity	NPC471737
0.7882	Intermediate Similarity	NPC474778
0.7882	Intermediate Similarity	NPC20688
0.7882	Intermediate Similarity	NPC474732
0.7882	Intermediate Similarity	NPC472986
0.7882	Intermediate Similarity	NPC472488
0.7882	Intermediate Similarity	NPC229717
0.7882	Intermediate Similarity	NPC51014
0.7882	Intermediate Similarity	NPC31564
0.7882	Intermediate Similarity	NPC472985
0.7882	Intermediate Similarity	NPC474733
0.7882	Intermediate Similarity	NPC72133
0.7875	Intermediate Similarity	NPC197659
0.7875	Intermediate Similarity	NPC472300
0.7875	Intermediate Similarity	NPC34110
0.7865	Intermediate Similarity	NPC245972
0.7865	Intermediate Similarity	NPC196485
0.7857	Intermediate Similarity	NPC476412
0.7857	Intermediate Similarity	NPC58841
0.7857	Intermediate Similarity	NPC161423
0.7857	Intermediate Similarity	NPC329043
0.7857	Intermediate Similarity	NPC227064
0.7857	Intermediate Similarity	NPC214043
0.7857	Intermediate Similarity	NPC85774
0.7857	Intermediate Similarity	NPC321187
0.7857	Intermediate Similarity	NPC96095
0.7857	Intermediate Similarity	NPC472480
0.7848	Intermediate Similarity	NPC279666
0.7848	Intermediate Similarity	NPC192540
0.7841	Intermediate Similarity	NPC26865
0.7841	Intermediate Similarity	NPC174167
0.7841	Intermediate Similarity	NPC475806
0.7841	Intermediate Similarity	NPC99380
0.7841	Intermediate Similarity	NPC470036
0.7831	Intermediate Similarity	NPC302661
0.7831	Intermediate Similarity	NPC151519
0.7831	Intermediate Similarity	NPC238991
0.7831	Intermediate Similarity	NPC320514
0.7816	Intermediate Similarity	NPC474918
0.7816	Intermediate Similarity	NPC76879
0.7816	Intermediate Similarity	NPC472973
0.7816	Intermediate Similarity	NPC119416
0.7816	Intermediate Similarity	NPC309603
0.7816	Intermediate Similarity	NPC473999
0.7816	Intermediate Similarity	NPC474245
0.7805	Intermediate Similarity	NPC37038
0.7805	Intermediate Similarity	NPC287063
0.7805	Intermediate Similarity	NPC472478
0.7805	Intermediate Similarity	NPC26139
0.7802	Intermediate Similarity	NPC18509
0.7792	Intermediate Similarity	NPC173321
0.7791	Intermediate Similarity	NPC475740
0.7791	Intermediate Similarity	NPC136948
0.7791	Intermediate Similarity	NPC58063
0.7778	Intermediate Similarity	NPC23778
0.7778	Intermediate Similarity	NPC80088
0.7778	Intermediate Similarity	NPC74410
0.7778	Intermediate Similarity	NPC253561
0.7778	Intermediate Similarity	NPC178852
0.7778	Intermediate Similarity	NPC474602
0.7765	Intermediate Similarity	NPC133954
0.7765	Intermediate Similarity	NPC29447
0.7765	Intermediate Similarity	NPC469948
0.7765	Intermediate Similarity	NPC478245
0.7765	Intermediate Similarity	NPC133652
0.7765	Intermediate Similarity	NPC474537
0.7753	Intermediate Similarity	NPC233118
0.7753	Intermediate Similarity	NPC263780
0.7753	Intermediate Similarity	NPC477436
0.7753	Intermediate Similarity	NPC12722
0.7753	Intermediate Similarity	NPC477435
0.775	Intermediate Similarity	NPC263582
0.775	Intermediate Similarity	NPC7629
0.775	Intermediate Similarity	NPC89294
0.775	Intermediate Similarity	NPC69143
0.775	Intermediate Similarity	NPC151622
0.775	Intermediate Similarity	NPC239758
0.775	Intermediate Similarity	NPC110725
0.7738	Intermediate Similarity	NPC102197
0.7727	Intermediate Similarity	NPC223093
0.7727	Intermediate Similarity	NPC113393
0.7727	Intermediate Similarity	NPC46441
0.7727	Intermediate Similarity	NPC85173
0.7722	Intermediate Similarity	NPC22134
0.7722	Intermediate Similarity	NPC251970
0.7722	Intermediate Similarity	NPC283908
0.7722	Intermediate Similarity	NPC476046
0.7722	Intermediate Similarity	NPC241854
0.7722	Intermediate Similarity	NPC103958
0.7722	Intermediate Similarity	NPC183503
0.7722	Intermediate Similarity	NPC161923
0.7711	Intermediate Similarity	NPC267691
0.7711	Intermediate Similarity	NPC328264
0.7711	Intermediate Similarity	NPC475863
0.7711	Intermediate Similarity	NPC263272
0.7711	Intermediate Similarity	NPC477372
0.7711	Intermediate Similarity	NPC3915

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 NPC476808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2007
0.2-0.3	4202
0.3-0.4	1916
0.4-0.5	459
0.5-0.6	116
0.6-0.7	154
0.7-0.8	88
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.92	High Similarity	NPD3617	Approved
0.8718	High Similarity	NPD4695	Discontinued
0.8519	High Similarity	NPD4197	Approved
0.8415	Intermediate Similarity	NPD5329	Approved
0.8272	Intermediate Similarity	NPD4221	Approved
0.8272	Intermediate Similarity	NPD4223	Phase 3
0.8095	Intermediate Similarity	NPD4694	Approved
0.8095	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3618	Phase 1
0.8095	Intermediate Similarity	NPD5280	Approved
0.8095	Intermediate Similarity	NPD5690	Phase 2
0.8023	Intermediate Similarity	NPD4753	Phase 2
0.8023	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4688	Approved
0.7882	Intermediate Similarity	NPD4693	Phase 3
0.7882	Intermediate Similarity	NPD4519	Discontinued
0.7882	Intermediate Similarity	NPD4690	Approved
0.7882	Intermediate Similarity	NPD4623	Approved
0.7882	Intermediate Similarity	NPD4689	Approved
0.7882	Intermediate Similarity	NPD5205	Approved
0.7882	Intermediate Similarity	NPD4138	Approved
0.7857	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD3133	Approved
0.7857	Intermediate Similarity	NPD3666	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7816	Intermediate Similarity	NPD5328	Approved
0.7802	Intermediate Similarity	NPD4755	Approved
0.7753	Intermediate Similarity	NPD4202	Approved
0.7711	Intermediate Similarity	NPD4692	Approved
0.7711	Intermediate Similarity	NPD4139	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD5222	Approved
0.7692	Intermediate Similarity	NPD5221	Approved
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7647	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD6079	Approved
0.764	Intermediate Similarity	NPD7515	Phase 2
0.7634	Intermediate Similarity	NPD4696	Approved
0.7634	Intermediate Similarity	NPD5286	Approved
0.7634	Intermediate Similarity	NPD4700	Approved
0.7634	Intermediate Similarity	NPD5285	Approved
0.7609	Intermediate Similarity	NPD5173	Approved
0.76	Intermediate Similarity	NPD7341	Phase 2
0.7586	Intermediate Similarity	NPD3573	Approved
0.7582	Intermediate Similarity	NPD4629	Approved
0.7582	Intermediate Similarity	NPD5210	Approved
0.7556	Intermediate Similarity	NPD5133	Approved
0.7553	Intermediate Similarity	NPD5223	Approved
0.7474	Intermediate Similarity	NPD5225	Approved
0.7474	Intermediate Similarity	NPD5224	Approved
0.7474	Intermediate Similarity	NPD5211	Phase 2
0.7474	Intermediate Similarity	NPD5226	Approved
0.7474	Intermediate Similarity	NPD4633	Approved
0.7473	Intermediate Similarity	NPD7748	Approved
0.747	Intermediate Similarity	NPD4195	Approved
0.7436	Intermediate Similarity	NPD4137	Phase 3
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD6080	Approved
0.7416	Intermediate Similarity	NPD6673	Approved
0.7396	Intermediate Similarity	NPD4754	Approved
0.7396	Intermediate Similarity	NPD5174	Approved
0.7396	Intermediate Similarity	NPD5175	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7342	Intermediate Similarity	NPD4747	Approved
0.7342	Intermediate Similarity	NPD4691	Approved
0.734	Intermediate Similarity	NPD5696	Approved
0.7326	Intermediate Similarity	NPD4788	Approved
0.732	Intermediate Similarity	NPD5141	Approved
0.7308	Intermediate Similarity	NPD5360	Phase 3
0.7308	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD6098	Approved
0.7253	Intermediate Similarity	NPD5281	Approved
0.7253	Intermediate Similarity	NPD5284	Approved
0.7253	Intermediate Similarity	NPD5693	Phase 1
0.7245	Intermediate Similarity	NPD6402	Approved
0.7245	Intermediate Similarity	NPD4767	Approved
0.7245	Intermediate Similarity	NPD5739	Approved
0.7245	Intermediate Similarity	NPD6675	Approved
0.7245	Intermediate Similarity	NPD4768	Approved
0.7245	Intermediate Similarity	NPD7128	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD7902	Approved
0.7172	Intermediate Similarity	NPD5697	Approved
0.7172	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD4096	Approved
0.7113	Intermediate Similarity	NPD5091	Approved
0.7111	Intermediate Similarity	NPD5208	Approved
0.71	Intermediate Similarity	NPD6011	Approved
0.71	Intermediate Similarity	NPD4730	Approved
0.71	Intermediate Similarity	NPD6899	Approved
0.71	Intermediate Similarity	NPD5128	Approved
0.71	Intermediate Similarity	NPD6881	Approved
0.71	Intermediate Similarity	NPD7320	Approved
0.71	Intermediate Similarity	NPD4729	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7073	Intermediate Similarity	NPD4058	Approved
0.7065	Intermediate Similarity	NPD5694	Approved
0.7065	Intermediate Similarity	NPD6050	Approved
0.7051	Intermediate Similarity	NPD7331	Phase 2
0.7037	Intermediate Similarity	NPD4758	Discontinued
0.703	Intermediate Similarity	NPD6373	Approved
0.703	Intermediate Similarity	NPD6372	Approved
0.703	Intermediate Similarity	NPD6013	Approved
0.703	Intermediate Similarity	NPD6014	Approved
0.703	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6399	Phase 3
0.6966	Remote Similarity	NPD1696	Phase 3
0.6961	Remote Similarity	NPD5247	Approved
0.6961	Remote Similarity	NPD5135	Approved
0.6961	Remote Similarity	NPD7102	Approved
0.6961	Remote Similarity	NPD5249	Phase 3
0.6961	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4634	Approved
0.6961	Remote Similarity	NPD6883	Approved
0.6961	Remote Similarity	NPD5251	Approved
0.6961	Remote Similarity	NPD5248	Approved
0.6961	Remote Similarity	NPD5169	Approved
0.6961	Remote Similarity	NPD7290	Approved
0.6961	Remote Similarity	NPD5250	Approved
0.6947	Remote Similarity	NPD7614	Phase 1
0.6931	Remote Similarity	NPD5168	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4518	Approved
0.6915	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD6001	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4789	Approved
0.6893	Remote Similarity	NPD6869	Approved
0.6893	Remote Similarity	NPD5127	Approved
0.6893	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5215	Approved
0.6893	Remote Similarity	NPD5217	Approved
0.6893	Remote Similarity	NPD6649	Approved
0.6893	Remote Similarity	NPD8130	Phase 1
0.6893	Remote Similarity	NPD6617	Approved
0.6893	Remote Similarity	NPD6847	Approved
0.6893	Remote Similarity	NPD5216	Approved
0.6893	Remote Similarity	NPD6650	Approved
0.6883	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4687	Approved
0.6867	Remote Similarity	NPD5733	Approved
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5654	Approved
0.6835	Remote Similarity	NPD4224	Phase 2
0.6829	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4243	Approved
0.6829	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5276	Approved
0.6827	Remote Similarity	NPD6882	Approved
0.6827	Remote Similarity	NPD8297	Approved
0.6782	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5207	Approved
0.6762	Remote Similarity	NPD4632	Approved
0.6709	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5959	Approved
0.6698	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD4784	Approved
0.6636	Remote Similarity	NPD6274	Approved
0.6629	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3704	Approved
0.6591	Remote Similarity	NPD4748	Discontinued
0.6591	Remote Similarity	NPD7525	Registered
0.6588	Remote Similarity	NPD6942	Approved
0.6588	Remote Similarity	NPD4190	Phase 3
0.6588	Remote Similarity	NPD7339	Approved
0.6588	Remote Similarity	NPD3703	Phase 2
0.6588	Remote Similarity	NPD5275	Approved
0.6585	Remote Similarity	NPD3698	Phase 2
0.6574	Remote Similarity	NPD6317	Approved
0.6574	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD5364	Discontinued
0.6538	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8028	Phase 2
0.6514	Remote Similarity	NPD6335	Approved
0.6514	Remote Similarity	NPD6314	Approved
0.6514	Remote Similarity	NPD6313	Approved
0.6506	Remote Similarity	NPD4244	Approved
0.6506	Remote Similarity	NPD4245	Approved
0.6481	Remote Similarity	NPD6868	Approved
0.6476	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)

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