NPASS Compound

Structure

NPC162164 OpenBabel07101718302D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.6888 -4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -2.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7229 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 1 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 18 4 1 1 0 0 0 19 5 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.268
LogD:	3.11
LogS:	-3.849
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	4.513
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.942
MDCK Permeability:	1.901317409647163e-05
Pgp-inhibitor:	0.29
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	85.57759857177734%
Volume Distribution (VD):	0.922
Pgp-substrate:	12.862146377563477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.628
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.416

ADMET: Excretion

Clearance (CL):	6.388
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.47
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.076
Carcinogencity:	0.057
Eye Corrosion:	0.546
Eye Irritation:	0.295
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC162164

Natural Product ID:	NPC162164
*Common Name:**	8Beta-Hydroxy-3-Oxopimara-15-Ene
IUPAC Name:	(4aS,4bR,7S,8aR,10aR)-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-4,4b,5,6,8,9,10,10a-octahydro-3H-phenanthren-2-one
Synonyms:
Standard InCHIKey:	QFWORCWEUCFUNT-SBCNTATESA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-18(4)10-7-15-19(5)11-9-16(21)17(2,3)14(19)8-12-20(15,22)13-18/h6,14-15,22H,1,7-13H2,2-5H3/t14-,15+,18-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H]2[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@]2(C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094091
PubChem CID:	46887197
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[557974]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[557974]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[557974]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[557974]

☑ 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 NPC162164 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	177
0.1-0.2	1778
0.2-0.3	7772
0.3-0.4	16396
0.4-0.5	7188
0.5-0.6	5271
0.6-0.7	3109
0.7-0.8	972
0.8-0.85	23
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC38426
0.9437	High Similarity	NPC104806
0.9306	High Similarity	NPC472746
0.8816	High Similarity	NPC473217
0.8684	High Similarity	NPC469637
0.8649	High Similarity	NPC198473
0.8571	High Similarity	NPC20096
0.8571	High Similarity	NPC48673
0.8472	Intermediate Similarity	NPC163020
0.8451	Intermediate Similarity	NPC2648
0.8442	Intermediate Similarity	NPC476809
0.8429	Intermediate Similarity	NPC103734
0.8378	Intermediate Similarity	NPC255168
0.8375	Intermediate Similarity	NPC224345
0.8333	Intermediate Similarity	NPC210323
0.8312	Intermediate Similarity	NPC215843
0.8243	Intermediate Similarity	NPC177826
0.8148	Intermediate Similarity	NPC133954
0.8133	Intermediate Similarity	NPC18819
0.8133	Intermediate Similarity	NPC46610
0.8125	Intermediate Similarity	NPC475726
0.8125	Intermediate Similarity	NPC472743
0.8108	Intermediate Similarity	NPC247195
0.8101	Intermediate Similarity	NPC328264
0.8077	Intermediate Similarity	NPC231431
0.8072	Intermediate Similarity	NPC193360
0.8056	Intermediate Similarity	NPC117607
0.8056	Intermediate Similarity	NPC101307
0.8056	Intermediate Similarity	NPC88454
0.8056	Intermediate Similarity	NPC263161
0.8052	Intermediate Similarity	NPC66105
0.8052	Intermediate Similarity	NPC149249
0.8049	Intermediate Similarity	NPC213412
0.8049	Intermediate Similarity	NPC475862
0.8049	Intermediate Similarity	NPC74363
0.8028	Intermediate Similarity	NPC64123
0.8028	Intermediate Similarity	NPC230047
0.8028	Intermediate Similarity	NPC19311
0.8026	Intermediate Similarity	NPC201027
0.8025	Intermediate Similarity	NPC475745
0.8025	Intermediate Similarity	NPC251170
0.8025	Intermediate Similarity	NPC474482
0.8	Intermediate Similarity	NPC473167
0.8	Intermediate Similarity	NPC36310
0.8	Intermediate Similarity	NPC81759
0.8	Intermediate Similarity	NPC48362
0.7975	Intermediate Similarity	NPC37038
0.7952	Intermediate Similarity	NPC471792
0.7952	Intermediate Similarity	NPC73064
0.7949	Intermediate Similarity	NPC275494
0.7949	Intermediate Similarity	NPC471409
0.7949	Intermediate Similarity	NPC476808
0.7945	Intermediate Similarity	NPC475977
0.7945	Intermediate Similarity	NPC94192
0.7927	Intermediate Similarity	NPC76518
0.7927	Intermediate Similarity	NPC292553
0.7927	Intermediate Similarity	NPC469993
0.7901	Intermediate Similarity	NPC291320
0.7901	Intermediate Similarity	NPC471036
0.7895	Intermediate Similarity	NPC22134
0.7875	Intermediate Similarity	NPC471898
0.7875	Intermediate Similarity	NPC162632
0.7875	Intermediate Similarity	NPC142244
0.7875	Intermediate Similarity	NPC3915
0.7875	Intermediate Similarity	NPC263272
0.7875	Intermediate Similarity	NPC274050
0.7875	Intermediate Similarity	NPC164210
0.7875	Intermediate Similarity	NPC267691
0.7857	Intermediate Similarity	NPC472802
0.7848	Intermediate Similarity	NPC474113
0.7848	Intermediate Similarity	NPC201459
0.7848	Intermediate Similarity	NPC192744
0.7848	Intermediate Similarity	NPC476812
0.7831	Intermediate Similarity	NPC158393
0.7831	Intermediate Similarity	NPC72638
0.7831	Intermediate Similarity	NPC235341
0.7831	Intermediate Similarity	NPC73038
0.7831	Intermediate Similarity	NPC472738
0.7831	Intermediate Similarity	NPC477579
0.7831	Intermediate Similarity	NPC95594
0.7821	Intermediate Similarity	NPC471035
0.7821	Intermediate Similarity	NPC476811
0.7821	Intermediate Similarity	NPC106078
0.7821	Intermediate Similarity	NPC212661
0.7821	Intermediate Similarity	NPC471897
0.7821	Intermediate Similarity	NPC266193
0.7821	Intermediate Similarity	NPC471899
0.7821	Intermediate Similarity	NPC107039
0.7821	Intermediate Similarity	NPC257666
0.7808	Intermediate Similarity	NPC41542
0.7805	Intermediate Similarity	NPC180834
0.7805	Intermediate Similarity	NPC264665
0.7805	Intermediate Similarity	NPC146683
0.7805	Intermediate Similarity	NPC474233
0.7805	Intermediate Similarity	NPC74595
0.7792	Intermediate Similarity	NPC279666
0.7792	Intermediate Similarity	NPC192540
0.7792	Intermediate Similarity	NPC39362
0.7791	Intermediate Similarity	NPC272746
0.7778	Intermediate Similarity	NPC310989
0.7778	Intermediate Similarity	NPC251779
0.7778	Intermediate Similarity	NPC145143
0.7778	Intermediate Similarity	NPC110780
0.7778	Intermediate Similarity	NPC69101
0.7778	Intermediate Similarity	NPC163236
0.7765	Intermediate Similarity	NPC69627
0.7765	Intermediate Similarity	NPC68148
0.7765	Intermediate Similarity	NPC475108
0.7765	Intermediate Similarity	NPC65615
0.7763	Intermediate Similarity	NPC68426
0.7763	Intermediate Similarity	NPC282905
0.7763	Intermediate Similarity	NPC161187
0.7763	Intermediate Similarity	NPC330659
0.7763	Intermediate Similarity	NPC244708
0.7763	Intermediate Similarity	NPC477229
0.7763	Intermediate Similarity	NPC232112
0.775	Intermediate Similarity	NPC2482
0.775	Intermediate Similarity	NPC164999
0.7738	Intermediate Similarity	NPC130577
0.7738	Intermediate Similarity	NPC102683
0.7738	Intermediate Similarity	NPC98442
0.7738	Intermediate Similarity	NPC88716
0.7738	Intermediate Similarity	NPC171203
0.7738	Intermediate Similarity	NPC293564
0.7738	Intermediate Similarity	NPC57469
0.7738	Intermediate Similarity	NPC469317
0.7738	Intermediate Similarity	NPC307426
0.7738	Intermediate Similarity	NPC142415
0.7738	Intermediate Similarity	NPC68160
0.7738	Intermediate Similarity	NPC469314
0.7738	Intermediate Similarity	NPC51700
0.7738	Intermediate Similarity	NPC141292
0.7738	Intermediate Similarity	NPC242468
0.7738	Intermediate Similarity	NPC241875
0.7738	Intermediate Similarity	NPC18064
0.7738	Intermediate Similarity	NPC4643
0.7722	Intermediate Similarity	NPC179028
0.7722	Intermediate Similarity	NPC260385
0.7722	Intermediate Similarity	NPC476810
0.7722	Intermediate Similarity	NPC280654
0.7722	Intermediate Similarity	NPC110094
0.7711	Intermediate Similarity	NPC470574
0.7711	Intermediate Similarity	NPC474537
0.7711	Intermediate Similarity	NPC190704
0.7711	Intermediate Similarity	NPC471034
0.7711	Intermediate Similarity	NPC264317
0.7711	Intermediate Similarity	NPC294438
0.7703	Intermediate Similarity	NPC473225
0.7703	Intermediate Similarity	NPC290445
0.7703	Intermediate Similarity	NPC36616
0.7692	Intermediate Similarity	NPC246445
0.7692	Intermediate Similarity	NPC186554
0.7692	Intermediate Similarity	NPC76966
0.7692	Intermediate Similarity	NPC20466
0.7692	Intermediate Similarity	NPC69143
0.7692	Intermediate Similarity	NPC89294
0.7692	Intermediate Similarity	NPC78935
0.7683	Intermediate Similarity	NPC53733
0.7683	Intermediate Similarity	NPC471037
0.7683	Intermediate Similarity	NPC118800
0.7683	Intermediate Similarity	NPC70834
0.7674	Intermediate Similarity	NPC126993
0.7674	Intermediate Similarity	NPC85173
0.7674	Intermediate Similarity	NPC46758
0.7674	Intermediate Similarity	NPC291028
0.7662	Intermediate Similarity	NPC183503
0.7662	Intermediate Similarity	NPC283908
0.7662	Intermediate Similarity	NPC159325
0.7662	Intermediate Similarity	NPC241854
0.7662	Intermediate Similarity	NPC168511
0.7662	Intermediate Similarity	NPC103958
0.7662	Intermediate Similarity	NPC476046
0.7662	Intermediate Similarity	NPC161923
0.7662	Intermediate Similarity	NPC251970
0.7654	Intermediate Similarity	NPC14151
0.7654	Intermediate Similarity	NPC103754
0.7654	Intermediate Similarity	NPC474484
0.7654	Intermediate Similarity	NPC147066
0.7654	Intermediate Similarity	NPC278459
0.7647	Intermediate Similarity	NPC473242
0.7647	Intermediate Similarity	NPC206060
0.7647	Intermediate Similarity	NPC472739
0.7647	Intermediate Similarity	NPC246708
0.7647	Intermediate Similarity	NPC471793
0.7647	Intermediate Similarity	NPC52169
0.7647	Intermediate Similarity	NPC48107
0.7647	Intermediate Similarity	NPC292491
0.7647	Intermediate Similarity	NPC17733
0.7647	Intermediate Similarity	NPC310752
0.7647	Intermediate Similarity	NPC40552
0.7647	Intermediate Similarity	NPC474677
0.7647	Intermediate Similarity	NPC474512
0.7647	Intermediate Similarity	NPC474719
0.7647	Intermediate Similarity	NPC470629
0.7647	Intermediate Similarity	NPC290690
0.7647	Intermediate Similarity	NPC182797
0.7647	Intermediate Similarity	NPC471791
0.7647	Intermediate Similarity	NPC181225
0.764	Intermediate Similarity	NPC160056
0.7632	Intermediate Similarity	NPC320549

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 NPC162164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	2263
0.2-0.3	4191
0.3-0.4	1718
0.4-0.5	415
0.5-0.6	183
0.6-0.7	147
0.7-0.8	45
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
0.8194	Intermediate Similarity	NPD5360	Phase 3
0.8194	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4788	Approved
0.7632	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4758	Discontinued
0.7632	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4786	Approved
0.7586	Intermediate Similarity	NPD6079	Approved
0.7586	Intermediate Similarity	NPD7515	Phase 2
0.7561	Intermediate Similarity	NPD4223	Phase 3
0.7561	Intermediate Similarity	NPD4221	Approved
0.7561	Intermediate Similarity	NPD3667	Approved
0.7558	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7432	Intermediate Similarity	NPD4224	Phase 2
0.7416	Intermediate Similarity	NPD7748	Approved
0.7412	Intermediate Similarity	NPD4519	Discontinued
0.7412	Intermediate Similarity	NPD4623	Approved
0.7381	Intermediate Similarity	NPD4197	Approved
0.7342	Intermediate Similarity	NPD3703	Phase 2
0.7326	Intermediate Similarity	NPD3573	Approved
0.7317	Intermediate Similarity	NPD4695	Discontinued
0.7303	Intermediate Similarity	NPD4202	Approved
0.7284	Intermediate Similarity	NPD5364	Discontinued
0.7284	Intermediate Similarity	NPD3617	Approved
0.7273	Intermediate Similarity	NPD4245	Approved
0.7273	Intermediate Similarity	NPD4789	Approved
0.7273	Intermediate Similarity	NPD4244	Approved
0.725	Intermediate Similarity	NPD6117	Approved
0.7215	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4138	Approved
0.7209	Intermediate Similarity	NPD4690	Approved
0.7209	Intermediate Similarity	NPD4688	Approved
0.7209	Intermediate Similarity	NPD4689	Approved
0.7209	Intermediate Similarity	NPD4693	Phase 3
0.7209	Intermediate Similarity	NPD5690	Phase 2
0.7209	Intermediate Similarity	NPD5205	Approved
0.7191	Intermediate Similarity	NPD8035	Phase 2
0.7191	Intermediate Similarity	NPD8034	Phase 2
0.7179	Intermediate Similarity	NPD6081	Approved
0.7176	Intermediate Similarity	NPD3133	Approved
0.7176	Intermediate Similarity	NPD3665	Phase 1
0.7176	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD7902	Approved
0.716	Intermediate Similarity	NPD6116	Phase 1
0.7159	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3698	Phase 2
0.7108	Intermediate Similarity	NPD7525	Registered
0.7073	Intermediate Similarity	NPD6118	Approved
0.7073	Intermediate Similarity	NPD6115	Approved
0.7073	Intermediate Similarity	NPD6114	Approved
0.7073	Intermediate Similarity	NPD6697	Approved
0.7067	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD5221	Approved
0.7024	Intermediate Similarity	NPD4692	Approved
0.7024	Intermediate Similarity	NPD4139	Approved
0.7021	Intermediate Similarity	NPD5285	Approved
0.7021	Intermediate Similarity	NPD4696	Approved
0.7021	Intermediate Similarity	NPD5286	Approved
0.7011	Intermediate Similarity	NPD4694	Approved
0.7011	Intermediate Similarity	NPD5280	Approved
0.6989	Remote Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD5173	Approved
0.6988	Remote Similarity	NPD4195	Approved
0.6988	Remote Similarity	NPD7645	Phase 2
0.6977	Remote Similarity	NPD3668	Phase 3
0.6966	Remote Similarity	NPD4753	Phase 2
0.6947	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6882	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.6875	Remote Similarity	NPD5211	Phase 2
0.6867	Remote Similarity	NPD3671	Phase 1
0.6848	Remote Similarity	NPD7900	Approved
0.6848	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD6098	Approved
0.6813	Remote Similarity	NPD5284	Approved
0.6813	Remote Similarity	NPD5281	Approved
0.6804	Remote Similarity	NPD5174	Approved
0.6804	Remote Similarity	NPD5175	Approved
0.679	Remote Similarity	NPD4784	Approved
0.679	Remote Similarity	NPD4785	Approved
0.6774	Remote Similarity	NPD4629	Approved
0.6774	Remote Similarity	NPD5210	Approved
0.675	Remote Similarity	NPD4243	Approved
0.6735	Remote Similarity	NPD5141	Approved
0.6709	Remote Similarity	NPD4137	Phase 3
0.6702	Remote Similarity	NPD7614	Phase 1
0.67	Remote Similarity	NPD6881	Approved
0.67	Remote Similarity	NPD6899	Approved
0.67	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6633	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD6084	Phase 2
0.6632	Remote Similarity	NPD6083	Phase 2
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD5279	Phase 3
0.6629	Remote Similarity	NPD5330	Approved
0.6625	Remote Similarity	NPD4747	Approved
0.6625	Remote Similarity	NPD4691	Approved
0.6623	Remote Similarity	NPD7341	Phase 2
0.66	Remote Similarity	NPD5697	Approved
0.6596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6673	Approved
0.6593	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD6904	Approved
0.6585	Remote Similarity	NPD4058	Approved
0.6582	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7290	Approved
0.6569	Remote Similarity	NPD7102	Approved
0.6569	Remote Similarity	NPD6883	Approved
0.6562	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD5133	Approved
0.6543	Remote Similarity	NPD5777	Approved
0.6538	Remote Similarity	NPD7331	Phase 2
0.6535	Remote Similarity	NPD4729	Approved
0.6535	Remote Similarity	NPD4730	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6535	Remote Similarity	NPD7320	Approved
0.6522	Remote Similarity	NPD4096	Approved
0.6506	Remote Similarity	NPD3702	Approved
0.6506	Remote Similarity	NPD6942	Approved
0.6506	Remote Similarity	NPD7339	Approved
0.6505	Remote Similarity	NPD6617	Approved
0.6505	Remote Similarity	NPD6649	Approved
0.6505	Remote Similarity	NPD6869	Approved
0.6505	Remote Similarity	NPD6847	Approved
0.6505	Remote Similarity	NPD6650	Approved
0.6505	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4768	Approved
0.65	Remote Similarity	NPD4767	Approved
0.6495	Remote Similarity	NPD7639	Approved
0.6495	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD6001	Approved
0.6484	Remote Similarity	NPD5208	Approved
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6484	Remote Similarity	NPD4518	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6442	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD8297	Approved
0.6436	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5695	Phase 3
0.6408	Remote Similarity	NPD5250	Approved
0.6408	Remote Similarity	NPD5169	Approved
0.6408	Remote Similarity	NPD5248	Approved
0.6408	Remote Similarity	NPD5135	Approved
0.6408	Remote Similarity	NPD5249	Phase 3
0.6408	Remote Similarity	NPD4634	Approved
0.6408	Remote Similarity	NPD5247	Approved
0.6408	Remote Similarity	NPD5251	Approved
0.6408	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5696	Approved
0.6386	Remote Similarity	NPD5733	Approved
0.6386	Remote Similarity	NPD4687	Approved
0.6373	Remote Similarity	NPD5128	Approved
0.6373	Remote Similarity	NPD5168	Approved
0.6364	Remote Similarity	NPD5091	Approved
0.6346	Remote Similarity	NPD5217	Approved
0.6346	Remote Similarity	NPD5127	Approved
0.6346	Remote Similarity	NPD5215	Approved
0.6346	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5216	Approved
0.6344	Remote Similarity	NPD5207	Approved
0.631	Remote Similarity	NPD5275	Approved
0.631	Remote Similarity	NPD4190	Phase 3
0.6277	Remote Similarity	NPD6411	Approved
0.6277	Remote Similarity	NPD5693	Phase 1
0.6277	Remote Similarity	NPD6050	Approved
0.6277	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD8028	Phase 2
0.6226	Remote Similarity	NPD4632	Approved
0.622	Remote Similarity	NPD4787	Phase 1
0.6204	Remote Similarity	NPD7115	Discovery

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