NPASS Compound

Structure

NPC81759 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 -0.3827 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 -3.4641 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 -0.0000 2.0000 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 -2.5981 0.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 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 -0.8660 1.5000 0.0000 C 0 0 1 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 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9641 3.8660 0.0000 O 0 0 0 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 -3.9641 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 4 1 1 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 18 3 1 1 0 0 0 19 8 1 1 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	343.985
LogP:	3.03
LogD:	2.562
LogS:	-1.712
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	5.654
Fsp3:	0.95
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:	-5.211
MDCK Permeability:	6.487466635007877e-06
Pgp-inhibitor:	0.721
Pgp-substrate:	0.229
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	73.1877212524414%
Volume Distribution (VD):	0.75
Pgp-substrate:	13.696477890014648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	11.036
Half-life (T1/2):	0.591

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.191
Maximum Recommended Daily Dose:	0.754
Skin Sensitization:	0.454
Carcinogencity:	0.961
Eye Corrosion:	0.028
Eye Irritation:	0.038
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC81759

Natural Product ID:	NPC81759
*Common Name:**	GFMRAAZMCOCUCY-JTZLQOMOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GFMRAAZMCOCUCY-JTZLQOMOSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-17(2)14-5-9-19-8-4-13(20(23,11-19)12-21)10-15(19)18(14,3)7-6-16(17)22/h13-15,21,23H,4-12H2,1-3H3/t13-,14+,15-,18+,19+,20+/m0/s1
SMILES:	OC[C@]1(O)C[C@@]23CC[C@H]1C[C@H]3[C@]1([C@H](CC2)C(C)(C)C(=O)CC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459910
PubChem CID:	21726550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003401] Villanovane, atisane, trachylobane or helvifulvane diterpenoids [CHEMONTID:0002738] Atisane 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
NPO15892	Euphorbia quinquecostata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350147]
NPO15892	Euphorbia quinquecostata	Species	Euphorbiaceae	Eukaryota	stem wood	n.a.	n.a.	PMID[8946746]
NPO15892	Euphorbia quinquecostata	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	66000.0	nM	PMID[460952]

☑ 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 NPC81759 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	435
0.1-0.2	3718
0.2-0.3	14108
0.3-0.4	12100
0.4-0.5	5027
0.5-0.6	4438
0.6-0.7	2282
0.7-0.8	529
0.8-0.85	30
0.85-0.9	11
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9143	High Similarity	NPC477229
0.9143	High Similarity	NPC282905
0.9143	High Similarity	NPC68426
0.9014	High Similarity	NPC159325
0.9014	High Similarity	NPC168511
0.8904	High Similarity	NPC23884
0.8889	High Similarity	NPC174964
0.8889	High Similarity	NPC267753
0.8889	High Similarity	NPC195155
0.8889	High Similarity	NPC97534
0.8841	High Similarity	NPC103647
0.8841	High Similarity	NPC260319
0.8841	High Similarity	NPC180777
0.8841	High Similarity	NPC2568
0.8767	High Similarity	NPC5767
0.8767	High Similarity	NPC475742
0.8767	High Similarity	NPC108840
0.875	High Similarity	NPC130011
0.8732	High Similarity	NPC247195
0.8676	High Similarity	NPC260116
0.8649	High Similarity	NPC221420
0.8611	High Similarity	NPC232112
0.8571	High Similarity	NPC475977
0.8493	Intermediate Similarity	NPC472854
0.8472	Intermediate Similarity	NPC320549
0.8472	Intermediate Similarity	NPC89310
0.8472	Intermediate Similarity	NPC290058
0.8472	Intermediate Similarity	NPC151018
0.8472	Intermediate Similarity	NPC156277
0.8472	Intermediate Similarity	NPC58057
0.8462	Intermediate Similarity	NPC269684
0.8451	Intermediate Similarity	NPC327728
0.8451	Intermediate Similarity	NPC213178
0.8451	Intermediate Similarity	NPC131892
0.8451	Intermediate Similarity	NPC6120
0.8442	Intermediate Similarity	NPC50658
0.8429	Intermediate Similarity	NPC472984
0.84	Intermediate Similarity	NPC143133
0.84	Intermediate Similarity	NPC298168
0.84	Intermediate Similarity	NPC475031
0.8378	Intermediate Similarity	NPC273366
0.831	Intermediate Similarity	NPC473225
0.831	Intermediate Similarity	NPC474954
0.831	Intermediate Similarity	NPC478228
0.831	Intermediate Similarity	NPC475893
0.8289	Intermediate Similarity	NPC472608
0.8289	Intermediate Similarity	NPC26029
0.8267	Intermediate Similarity	NPC472486
0.8267	Intermediate Similarity	NPC472487
0.825	Intermediate Similarity	NPC131350
0.8243	Intermediate Similarity	NPC254340
0.8205	Intermediate Similarity	NPC280781
0.8205	Intermediate Similarity	NPC476071
0.8205	Intermediate Similarity	NPC48756
0.8205	Intermediate Similarity	NPC12933
0.8169	Intermediate Similarity	NPC204233
0.8169	Intermediate Similarity	NPC41542
0.8158	Intermediate Similarity	NPC264602
0.8158	Intermediate Similarity	NPC472746
0.8143	Intermediate Similarity	NPC19311
0.8143	Intermediate Similarity	NPC80463
0.8143	Intermediate Similarity	NPC230047
0.8133	Intermediate Similarity	NPC212733
0.8133	Intermediate Similarity	NPC21220
0.8133	Intermediate Similarity	NPC27349
0.8133	Intermediate Similarity	NPC159789
0.8133	Intermediate Similarity	NPC24014
0.8133	Intermediate Similarity	NPC125767
0.8125	Intermediate Similarity	NPC25037
0.8125	Intermediate Similarity	NPC34984
0.8125	Intermediate Similarity	NPC474996
0.8125	Intermediate Similarity	NPC105895
0.8101	Intermediate Similarity	NPC268040
0.8101	Intermediate Similarity	NPC317066
0.8101	Intermediate Similarity	NPC61107
0.8101	Intermediate Similarity	NPC30583
0.8101	Intermediate Similarity	NPC289486
0.8082	Intermediate Similarity	NPC231945
0.8077	Intermediate Similarity	NPC470609
0.8056	Intermediate Similarity	NPC469724
0.8056	Intermediate Similarity	NPC31187
0.8056	Intermediate Similarity	NPC281203
0.8056	Intermediate Similarity	NPC100917
0.8052	Intermediate Similarity	NPC243594
0.8052	Intermediate Similarity	NPC31031
0.8026	Intermediate Similarity	NPC4209
0.8	Intermediate Similarity	NPC472743
0.8	Intermediate Similarity	NPC475726
0.8	Intermediate Similarity	NPC133922
0.8	Intermediate Similarity	NPC167702
0.8	Intermediate Similarity	NPC162164
0.8	Intermediate Similarity	NPC280026
0.7975	Intermediate Similarity	NPC328264
0.7949	Intermediate Similarity	NPC320144
0.7945	Intermediate Similarity	NPC324607
0.7945	Intermediate Similarity	NPC321732
0.7927	Intermediate Similarity	NPC80700
0.7927	Intermediate Similarity	NPC476726
0.7927	Intermediate Similarity	NPC476727
0.7922	Intermediate Similarity	NPC477919
0.7922	Intermediate Similarity	NPC112463
0.7922	Intermediate Similarity	NPC180199
0.7922	Intermediate Similarity	NPC149249
0.7922	Intermediate Similarity	NPC207010
0.7922	Intermediate Similarity	NPC317913
0.7917	Intermediate Similarity	NPC48079
0.791	Intermediate Similarity	NPC135438
0.7901	Intermediate Similarity	NPC237938
0.7901	Intermediate Similarity	NPC219535
0.7901	Intermediate Similarity	NPC475745
0.7901	Intermediate Similarity	NPC474482
0.7875	Intermediate Similarity	NPC121121
0.7867	Intermediate Similarity	NPC310766
0.7857	Intermediate Similarity	NPC290791
0.7857	Intermediate Similarity	NPC292419
0.7848	Intermediate Similarity	NPC261616
0.7838	Intermediate Similarity	NPC108131
0.7838	Intermediate Similarity	NPC476731
0.7831	Intermediate Similarity	NPC202937
0.7831	Intermediate Similarity	NPC263802
0.7831	Intermediate Similarity	NPC469317
0.7831	Intermediate Similarity	NPC241875
0.7831	Intermediate Similarity	NPC469314
0.7821	Intermediate Similarity	NPC80089
0.7821	Intermediate Similarity	NPC34046
0.7821	Intermediate Similarity	NPC224802
0.7821	Intermediate Similarity	NPC324700
0.7821	Intermediate Similarity	NPC185465
0.7821	Intermediate Similarity	NPC171426
0.7821	Intermediate Similarity	NPC476732
0.7821	Intermediate Similarity	NPC199965
0.7808	Intermediate Similarity	NPC472741
0.7805	Intermediate Similarity	NPC133954
0.7805	Intermediate Similarity	NPC62572
0.7805	Intermediate Similarity	NPC292553
0.7791	Intermediate Similarity	NPC472148
0.7791	Intermediate Similarity	NPC472147
0.7778	Intermediate Similarity	NPC142712
0.7778	Intermediate Similarity	NPC327451
0.7778	Intermediate Similarity	NPC472744
0.7765	Intermediate Similarity	NPC472146
0.7765	Intermediate Similarity	NPC185529
0.7763	Intermediate Similarity	NPC38426
0.775	Intermediate Similarity	NPC469745
0.775	Intermediate Similarity	NPC474870
0.775	Intermediate Similarity	NPC58631
0.775	Intermediate Similarity	NPC271572
0.7733	Intermediate Similarity	NPC473267
0.7722	Intermediate Similarity	NPC80891
0.7722	Intermediate Similarity	NPC245029
0.7722	Intermediate Similarity	NPC201276
0.7722	Intermediate Similarity	NPC476812
0.7722	Intermediate Similarity	NPC201459
0.7722	Intermediate Similarity	NPC31302
0.7711	Intermediate Similarity	NPC74363
0.7711	Intermediate Similarity	NPC472272
0.7711	Intermediate Similarity	NPC471737
0.7711	Intermediate Similarity	NPC213412
0.7711	Intermediate Similarity	NPC475862
0.7711	Intermediate Similarity	NPC83242
0.7711	Intermediate Similarity	NPC472738
0.7703	Intermediate Similarity	NPC252032
0.7703	Intermediate Similarity	NPC470830
0.7703	Intermediate Similarity	NPC469941
0.7703	Intermediate Similarity	NPC319671
0.7703	Intermediate Similarity	NPC299948
0.7703	Intermediate Similarity	NPC476734
0.7703	Intermediate Similarity	NPC254037
0.7703	Intermediate Similarity	NPC470833
0.7703	Intermediate Similarity	NPC241085
0.7703	Intermediate Similarity	NPC129829
0.7703	Intermediate Similarity	NPC107919
0.7703	Intermediate Similarity	NPC196197
0.7683	Intermediate Similarity	NPC264665
0.7683	Intermediate Similarity	NPC473299
0.7683	Intermediate Similarity	NPC74595
0.7683	Intermediate Similarity	NPC474233
0.7683	Intermediate Similarity	NPC50438
0.7671	Intermediate Similarity	NPC63190
0.7662	Intermediate Similarity	NPC72444
0.7662	Intermediate Similarity	NPC179858
0.7654	Intermediate Similarity	NPC328007
0.7647	Intermediate Similarity	NPC236588
0.7647	Intermediate Similarity	NPC220498
0.7625	Intermediate Similarity	NPC472853
0.7619	Intermediate Similarity	NPC73064
0.7619	Intermediate Similarity	NPC4643
0.7619	Intermediate Similarity	NPC57469
0.7619	Intermediate Similarity	NPC470920
0.76	Intermediate Similarity	NPC477929
0.76	Intermediate Similarity	NPC192192
0.7595	Intermediate Similarity	NPC478084
0.759	Intermediate Similarity	NPC264317
0.759	Intermediate Similarity	NPC294438
0.7586	Intermediate Similarity	NPC275809
0.7568	Intermediate Similarity	NPC469987
0.7564	Intermediate Similarity	NPC104806
0.7561	Intermediate Similarity	NPC292458
0.7561	Intermediate Similarity	NPC217559
0.7561	Intermediate Similarity	NPC268578

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 NPC81759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	523
0.1-0.2	3908
0.2-0.3	3282
0.3-0.4	920
0.4-0.5	254
0.5-0.6	208
0.6-0.7	31
0.7-0.8	24
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
0.8472	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD5360	Phase 3
0.8133	Intermediate Similarity	NPD3703	Phase 2
0.8082	Intermediate Similarity	NPD4244	Approved
0.8082	Intermediate Similarity	NPD4789	Approved
0.8082	Intermediate Similarity	NPD4245	Approved
0.8026	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3698	Phase 2
0.7922	Intermediate Similarity	NPD6116	Phase 1
0.7887	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6697	Approved
0.7821	Intermediate Similarity	NPD6118	Approved
0.7821	Intermediate Similarity	NPD6114	Approved
0.7821	Intermediate Similarity	NPD6115	Approved
0.7733	Intermediate Similarity	NPD4758	Discontinued
0.7703	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3671	Phase 1
0.759	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4224	Phase 2
0.7375	Intermediate Similarity	NPD5364	Discontinued
0.7273	Intermediate Similarity	NPD6081	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD4788	Approved
0.7051	Intermediate Similarity	NPD5777	Approved
0.7	Intermediate Similarity	NPD3702	Approved
0.6923	Remote Similarity	NPD4787	Phase 1
0.6923	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD3618	Phase 1
0.6889	Remote Similarity	NPD8035	Phase 2
0.6889	Remote Similarity	NPD8034	Phase 2
0.686	Remote Similarity	NPD4786	Approved
0.6854	Remote Similarity	NPD5328	Approved
0.6824	Remote Similarity	NPD3667	Approved
0.6703	Remote Similarity	NPD6079	Approved
0.6702	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.663	Remote Similarity	NPD4202	Approved
0.6477	Remote Similarity	NPD3133	Approved
0.6477	Remote Similarity	NPD3665	Phase 1
0.6477	Remote Similarity	NPD3666	Approved
0.6465	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7525	Registered
0.6383	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7900	Approved
0.6354	Remote Similarity	NPD4755	Approved
0.6353	Remote Similarity	NPD3617	Approved
0.6333	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4753	Phase 2
0.6275	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD615	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4223	Phase 3
0.6238	Remote Similarity	NPD6920	Discontinued
0.6224	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD5286	Approved
0.6224	Remote Similarity	NPD8418	Phase 2
0.6224	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD4696	Approved
0.6222	Remote Similarity	NPD5329	Approved
0.6214	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6928	Phase 2
0.6186	Remote Similarity	NPD5173	Approved
0.6176	Remote Similarity	NPD385	Approved
0.6176	Remote Similarity	NPD384	Approved
0.6162	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD371	Approved
0.6154	Remote Similarity	NPD7909	Approved
0.6136	Remote Similarity	NPD4692	Approved
0.6136	Remote Similarity	NPD4139	Approved
0.6129	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD4197	Approved
0.6105	Remote Similarity	NPD6399	Phase 3
0.61	Remote Similarity	NPD5225	Approved
0.61	Remote Similarity	NPD5211	Phase 2
0.61	Remote Similarity	NPD5226	Approved
0.61	Remote Similarity	NPD5224	Approved
0.61	Remote Similarity	NPD4633	Approved
0.6087	Remote Similarity	NPD3573	Approved
0.6078	Remote Similarity	NPD5739	Approved
0.6078	Remote Similarity	NPD7128	Approved
0.6078	Remote Similarity	NPD6675	Approved
0.6078	Remote Similarity	NPD6402	Approved
0.6053	Remote Similarity	NPD3198	Approved
0.604	Remote Similarity	NPD4754	Approved
0.604	Remote Similarity	NPD5174	Approved
0.604	Remote Similarity	NPD5175	Approved
0.6023	Remote Similarity	NPD4695	Discontinued
0.6022	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD4634	Approved
0.5981	Remote Similarity	NPD8133	Approved
0.598	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD4629	Approved
0.5979	Remote Similarity	NPD5210	Approved
0.5978	Remote Similarity	NPD4623	Approved
0.5978	Remote Similarity	NPD4138	Approved
0.5978	Remote Similarity	NPD4519	Discontinued
0.5978	Remote Similarity	NPD5279	Phase 3
0.5978	Remote Similarity	NPD4688	Approved
0.5978	Remote Similarity	NPD4693	Phase 3
0.5978	Remote Similarity	NPD5205	Approved
0.5978	Remote Similarity	NPD4690	Approved
0.5978	Remote Similarity	NPD4689	Approved
0.5963	Remote Similarity	NPD7115	Discovery
0.5963	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6415	Discontinued
0.5962	Remote Similarity	NPD7320	Approved
0.5962	Remote Similarity	NPD6899	Approved
0.5962	Remote Similarity	NPD6881	Approved
0.596	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD4768	Approved
0.5922	Remote Similarity	NPD4767	Approved
0.5905	Remote Similarity	NPD6372	Approved
0.5905	Remote Similarity	NPD6373	Approved
0.5905	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7640	Approved
0.59	Remote Similarity	NPD7639	Approved
0.5888	Remote Similarity	NPD8297	Approved
0.5865	Remote Similarity	NPD5701	Approved
0.5865	Remote Similarity	NPD6412	Phase 2
0.5865	Remote Similarity	NPD5697	Approved
0.5854	Remote Similarity	NPD6705	Phase 1
0.5849	Remote Similarity	NPD6883	Approved
0.5849	Remote Similarity	NPD7102	Approved
0.5849	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5824	Remote Similarity	NPD3669	Approved
0.5824	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7339	Approved
0.5814	Remote Similarity	NPD6942	Approved
0.581	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD5128	Approved
0.581	Remote Similarity	NPD4730	Approved
0.581	Remote Similarity	NPD4729	Approved
0.5806	Remote Similarity	NPD6409	Approved
0.5806	Remote Similarity	NPD5690	Phase 2
0.5806	Remote Similarity	NPD7521	Approved
0.5806	Remote Similarity	NPD5280	Approved
0.5806	Remote Similarity	NPD7334	Approved
0.5806	Remote Similarity	NPD7146	Approved
0.5806	Remote Similarity	NPD6684	Approved
0.5806	Remote Similarity	NPD4694	Approved
0.5806	Remote Similarity	NPD5330	Approved
0.5797	Remote Similarity	NPD388	Approved
0.5797	Remote Similarity	NPD386	Approved
0.5794	Remote Similarity	NPD6869	Approved
0.5794	Remote Similarity	NPD6649	Approved
0.5794	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6847	Approved
0.5794	Remote Similarity	NPD8130	Phase 1
0.5794	Remote Similarity	NPD6650	Approved
0.5794	Remote Similarity	NPD6617	Approved
0.5789	Remote Similarity	NPD8328	Phase 3
0.5784	Remote Similarity	NPD7632	Discontinued
0.5778	Remote Similarity	NPD1779	Approved
0.5778	Remote Similarity	NPD1780	Approved
0.5773	Remote Similarity	NPD8171	Discontinued
0.5758	Remote Similarity	NPD7614	Phase 1
0.5755	Remote Similarity	NPD6014	Approved
0.5755	Remote Similarity	NPD6012	Approved
0.5755	Remote Similarity	NPD6013	Approved
0.5747	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6933	Approved
0.5741	Remote Similarity	NPD6882	Approved
0.5727	Remote Similarity	NPD6940	Discontinued
0.5701	Remote Similarity	NPD5135	Approved
0.5701	Remote Similarity	NPD5250	Approved
0.5701	Remote Similarity	NPD5251	Approved
0.5701	Remote Similarity	NPD5248	Approved
0.5701	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5249	Phase 3
0.5701	Remote Similarity	NPD5169	Approved
0.5701	Remote Similarity	NPD5247	Approved
0.5698	Remote Similarity	NPD1810	Approved
0.5698	Remote Similarity	NPD1811	Approved
0.5684	Remote Similarity	NPD6903	Approved
0.5684	Remote Similarity	NPD6672	Approved
0.5684	Remote Similarity	NPD5737	Approved
0.5679	Remote Similarity	NPD7341	Phase 2
0.5667	Remote Similarity	NPD4748	Discontinued
0.566	Remote Similarity	NPD5168	Approved
0.5657	Remote Similarity	NPD5695	Phase 3
0.5657	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5215	Approved
0.5648	Remote Similarity	NPD5217	Approved
0.5648	Remote Similarity	NPD5216	Approved
0.5648	Remote Similarity	NPD5127	Approved
0.5644	Remote Similarity	NPD5696	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