NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	286.641
LogP:	3.552
LogD:	3.271
LogS:	-4.133
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	3.96
Fsp3:	0.75
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:	-4.615
MDCK Permeability:	2.2854317649034783e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.845
30% Bioavailability (F30%):	0.505

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	83.53325653076172%
Volume Distribution (VD):	0.891
Pgp-substrate:	20.95697021484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.733
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	6.095
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.719
Skin Sensitization:	0.947
Carcinogencity:	0.447
Eye Corrosion:	0.396
Eye Irritation:	0.213
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC20025

Natural Product ID:	NPC20025
*Common Name:**	Methyl Aignopsanoate
IUPAC Name:	methyl (2Z)-2-[(4aR,5S,8aS)-4a,5,8a-trimethyl-1-oxo-3,4,5,6,7,8-hexahydronaphthalen-2-ylidene]acetate
Synonyms:	Methyl Aignopsanoate
Standard InCHIKey:	CJQOKVDQHHONIF-USYVDOKNSA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-11-6-5-8-16(3)14(18)12(10-13(17)19-4)7-9-15(11,16)2/h10-11H,5-9H2,1-4H3/b12-10-/t11-,15+,16+/m0/s1
SMILES:	COC(=O)/C=C1/CC[C@]2([C@](C1=O)(C)CCC[C@@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934280
PubChem CID:	42631651
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003628] Alpha,beta-unsaturated carboxylic esters [CHEMONTID:0003626] Enoate esters

*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
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	Tongan	n.a.	PMID[19877653]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22129061]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30371079]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[516135]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[516135]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[516135]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2.5	ug.mL-1	PMID[516135]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	10.0	ug.mL-1	PMID[516135]

☑ 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 NPC20025 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	1523
0.2-0.3	6615
0.3-0.4	15817
0.4-0.5	8360
0.5-0.6	6778
0.6-0.7	2863
0.7-0.8	500
0.8-0.85	38
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC65650
0.8947	High Similarity	NPC94200
0.8873	High Similarity	NPC133253
0.8873	High Similarity	NPC21944
0.8831	High Similarity	NPC474976
0.8831	High Similarity	NPC474790
0.8696	High Similarity	NPC185587
0.859	High Similarity	NPC118423
0.8514	High Similarity	NPC476346
0.8493	Intermediate Similarity	NPC276336
0.8493	Intermediate Similarity	NPC180015
0.8493	Intermediate Similarity	NPC130016
0.8493	Intermediate Similarity	NPC56747
0.8493	Intermediate Similarity	NPC109576
0.8462	Intermediate Similarity	NPC268122
0.8462	Intermediate Similarity	NPC200513
0.84	Intermediate Similarity	NPC40353
0.8375	Intermediate Similarity	NPC189311
0.8333	Intermediate Similarity	NPC40228
0.8312	Intermediate Similarity	NPC190211
0.8289	Intermediate Similarity	NPC472300
0.8272	Intermediate Similarity	NPC168248
0.825	Intermediate Similarity	NPC475100
0.825	Intermediate Similarity	NPC149869
0.8194	Intermediate Similarity	NPC155198
0.8193	Intermediate Similarity	NPC474844
0.8182	Intermediate Similarity	NPC105197
0.8171	Intermediate Similarity	NPC477228
0.8171	Intermediate Similarity	NPC163016
0.8171	Intermediate Similarity	NPC75315
0.8158	Intermediate Similarity	NPC4509
0.8158	Intermediate Similarity	NPC27205
0.8158	Intermediate Similarity	NPC19907
0.8158	Intermediate Similarity	NPC473223
0.8148	Intermediate Similarity	NPC65661
0.8148	Intermediate Similarity	NPC86316
0.8148	Intermediate Similarity	NPC106416
0.8095	Intermediate Similarity	NPC476437
0.8095	Intermediate Similarity	NPC51486
0.8095	Intermediate Similarity	NPC476369
0.8049	Intermediate Similarity	NPC220478
0.8	Intermediate Similarity	NPC472867
0.8	Intermediate Similarity	NPC469805
0.8	Intermediate Similarity	NPC469806
0.8	Intermediate Similarity	NPC469804
0.8	Intermediate Similarity	NPC469799
0.8	Intermediate Similarity	NPC472239
0.7976	Intermediate Similarity	NPC5509
0.7975	Intermediate Similarity	NPC469797
0.7975	Intermediate Similarity	NPC469798
0.7973	Intermediate Similarity	NPC265782
0.7973	Intermediate Similarity	NPC251929
0.7973	Intermediate Similarity	NPC2634
0.7971	Intermediate Similarity	NPC127582
0.7949	Intermediate Similarity	NPC471220
0.7949	Intermediate Similarity	NPC470052
0.7949	Intermediate Similarity	NPC198240
0.7945	Intermediate Similarity	NPC188292
0.7945	Intermediate Similarity	NPC260474
0.7901	Intermediate Similarity	NPC279639
0.7901	Intermediate Similarity	NPC3856
0.7901	Intermediate Similarity	NPC193198
0.7901	Intermediate Similarity	NPC22611
0.7887	Intermediate Similarity	NPC329698
0.7882	Intermediate Similarity	NPC8062
0.7875	Intermediate Similarity	NPC229584
0.7875	Intermediate Similarity	NPC90055
0.7875	Intermediate Similarity	NPC14203
0.7867	Intermediate Similarity	NPC181587
0.7867	Intermediate Similarity	NPC54123
0.7857	Intermediate Similarity	NPC226863
0.7857	Intermediate Similarity	NPC196407
0.7857	Intermediate Similarity	NPC472302
0.7838	Intermediate Similarity	NPC139397
0.7831	Intermediate Similarity	NPC472863
0.7821	Intermediate Similarity	NPC165711
0.7821	Intermediate Similarity	NPC97377
0.7821	Intermediate Similarity	NPC61952
0.7821	Intermediate Similarity	NPC470557
0.7816	Intermediate Similarity	NPC476415
0.7805	Intermediate Similarity	NPC474359
0.7805	Intermediate Similarity	NPC16287
0.7805	Intermediate Similarity	NPC178025
0.7805	Intermediate Similarity	NPC30486
0.7805	Intermediate Similarity	NPC181743
0.7792	Intermediate Similarity	NPC244166
0.7792	Intermediate Similarity	NPC469803
0.7791	Intermediate Similarity	NPC177037
0.7791	Intermediate Similarity	NPC472814
0.7778	Intermediate Similarity	NPC142253
0.7778	Intermediate Similarity	NPC186276
0.7778	Intermediate Similarity	NPC251118
0.7778	Intermediate Similarity	NPC3511
0.7778	Intermediate Similarity	NPC107258
0.7765	Intermediate Similarity	NPC251528
0.7765	Intermediate Similarity	NPC174342
0.7765	Intermediate Similarity	NPC284561
0.7763	Intermediate Similarity	NPC474228
0.7763	Intermediate Similarity	NPC144947
0.7763	Intermediate Similarity	NPC303613
0.7746	Intermediate Similarity	NPC197238
0.7746	Intermediate Similarity	NPC288253
0.7746	Intermediate Similarity	NPC202118
0.7733	Intermediate Similarity	NPC260040
0.7733	Intermediate Similarity	NPC307176
0.7727	Intermediate Similarity	NPC209355
0.7722	Intermediate Similarity	NPC59436
0.7711	Intermediate Similarity	NPC60350
0.7703	Intermediate Similarity	NPC310992
0.7703	Intermediate Similarity	NPC87141
0.7701	Intermediate Similarity	NPC472871
0.7701	Intermediate Similarity	NPC139692
0.7701	Intermediate Similarity	NPC469939
0.7692	Intermediate Similarity	NPC474463
0.7692	Intermediate Similarity	NPC469796
0.7692	Intermediate Similarity	NPC469793
0.7692	Intermediate Similarity	NPC180886
0.7683	Intermediate Similarity	NPC469
0.7681	Intermediate Similarity	NPC60772
0.7674	Intermediate Similarity	NPC159748
0.7674	Intermediate Similarity	NPC101651
0.7674	Intermediate Similarity	NPC471818
0.7662	Intermediate Similarity	NPC166797
0.7662	Intermediate Similarity	NPC329866
0.7662	Intermediate Similarity	NPC309852
0.7662	Intermediate Similarity	NPC474797
0.7662	Intermediate Similarity	NPC474796
0.7654	Intermediate Similarity	NPC475833
0.7654	Intermediate Similarity	NPC278459
0.7654	Intermediate Similarity	NPC282293
0.7647	Intermediate Similarity	NPC472870
0.7647	Intermediate Similarity	NPC215831
0.7639	Intermediate Similarity	NPC52449
0.7639	Intermediate Similarity	NPC285371
0.7639	Intermediate Similarity	NPC469662
0.7639	Intermediate Similarity	NPC475124
0.7639	Intermediate Similarity	NPC212210
0.7639	Intermediate Similarity	NPC169275
0.7632	Intermediate Similarity	NPC190035
0.7632	Intermediate Similarity	NPC257618
0.7632	Intermediate Similarity	NPC474562
0.7625	Intermediate Similarity	NPC476177
0.7625	Intermediate Similarity	NPC150646
0.7625	Intermediate Similarity	NPC263951
0.7625	Intermediate Similarity	NPC471299
0.7614	Intermediate Similarity	NPC470697
0.7614	Intermediate Similarity	NPC84893
0.7606	Intermediate Similarity	NPC60565
0.76	Intermediate Similarity	NPC256846
0.7595	Intermediate Similarity	NPC316500
0.759	Intermediate Similarity	NPC87552
0.7586	Intermediate Similarity	NPC473986
0.7586	Intermediate Similarity	NPC474018
0.7586	Intermediate Similarity	NPC303697
0.7586	Intermediate Similarity	NPC477783
0.7586	Intermediate Similarity	NPC473944
0.7571	Intermediate Similarity	NPC472304
0.7571	Intermediate Similarity	NPC276764
0.7568	Intermediate Similarity	NPC4370
0.7568	Intermediate Similarity	NPC290350
0.7561	Intermediate Similarity	NPC302661
0.7561	Intermediate Similarity	NPC100297
0.7561	Intermediate Similarity	NPC16321
0.7561	Intermediate Similarity	NPC238991
0.7561	Intermediate Similarity	NPC142683
0.7561	Intermediate Similarity	NPC178676
0.7558	Intermediate Similarity	NPC73995
0.7558	Intermediate Similarity	NPC285982
0.7556	Intermediate Similarity	NPC253826
0.7556	Intermediate Similarity	NPC474343
0.7532	Intermediate Similarity	NPC251705
0.7531	Intermediate Similarity	NPC195424
0.7531	Intermediate Similarity	NPC267517
0.7529	Intermediate Similarity	NPC181327
0.7529	Intermediate Similarity	NPC476293
0.7529	Intermediate Similarity	NPC476409
0.7528	Intermediate Similarity	NPC33473
0.75	Intermediate Similarity	NPC159577
0.75	Intermediate Similarity	NPC239098
0.75	Intermediate Similarity	NPC475657
0.75	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC474680
0.75	Intermediate Similarity	NPC115515
0.75	Intermediate Similarity	NPC115021
0.75	Intermediate Similarity	NPC323765
0.75	Intermediate Similarity	NPC74410
0.75	Intermediate Similarity	NPC242069
0.75	Intermediate Similarity	NPC177932
0.75	Intermediate Similarity	NPC476416
0.75	Intermediate Similarity	NPC35734
0.75	Intermediate Similarity	NPC472303
0.75	Intermediate Similarity	NPC217394
0.75	Intermediate Similarity	NPC282593
0.75	Intermediate Similarity	NPC110405
0.75	Intermediate Similarity	NPC8571
0.7473	Intermediate Similarity	NPC316598
0.7473	Intermediate Similarity	NPC57079
0.7473	Intermediate Similarity	NPC108368
0.7471	Intermediate Similarity	NPC152467
0.7471	Intermediate Similarity	NPC477782

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 NPC20025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1695
0.2-0.3	4227
0.3-0.4	2155
0.4-0.5	513
0.5-0.6	249
0.6-0.7	107
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD4691	Approved
0.7838	Intermediate Similarity	NPD4137	Phase 3
0.7733	Intermediate Similarity	NPD4747	Approved
0.7662	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD1694	Approved
0.7412	Intermediate Similarity	NPD6684	Approved
0.7412	Intermediate Similarity	NPD7334	Approved
0.7412	Intermediate Similarity	NPD7521	Approved
0.7412	Intermediate Similarity	NPD7146	Approved
0.7412	Intermediate Similarity	NPD6409	Approved
0.7412	Intermediate Similarity	NPD5330	Approved
0.7403	Intermediate Similarity	NPD5276	Approved
0.7386	Intermediate Similarity	NPD5693	Phase 1
0.7326	Intermediate Similarity	NPD3573	Approved
0.7241	Intermediate Similarity	NPD6672	Approved
0.7241	Intermediate Similarity	NPD5737	Approved
0.7241	Intermediate Similarity	NPD6903	Approved
0.7241	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4687	Approved
0.7215	Intermediate Similarity	NPD5733	Approved
0.7125	Intermediate Similarity	NPD8039	Approved
0.7108	Intermediate Similarity	NPD4695	Discontinued
0.7045	Intermediate Similarity	NPD5208	Approved
0.6966	Remote Similarity	NPD6673	Approved
0.6966	Remote Similarity	NPD6080	Approved
0.6966	Remote Similarity	NPD6904	Approved
0.6944	Remote Similarity	NPD287	Approved
0.6941	Remote Similarity	NPD5209	Approved
0.6933	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7748	Approved
0.6848	Remote Similarity	NPD7900	Approved
0.6824	Remote Similarity	NPD8028	Phase 2
0.6818	Remote Similarity	NPD6098	Approved
0.6818	Remote Similarity	NPD4519	Discontinued
0.6818	Remote Similarity	NPD4623	Approved
0.6813	Remote Similarity	NPD7515	Phase 2
0.6782	Remote Similarity	NPD3666	Approved
0.6782	Remote Similarity	NPD3133	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.6774	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD4223	Phase 3
0.6737	Remote Similarity	NPD4225	Approved
0.6737	Remote Similarity	NPD7638	Approved
0.6703	Remote Similarity	NPD5692	Phase 3
0.6703	Remote Similarity	NPD5785	Approved
0.6703	Remote Similarity	NPD5207	Approved
0.6702	Remote Similarity	NPD7732	Phase 3
0.67	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6632	Remote Similarity	NPD7902	Approved
0.6632	Remote Similarity	NPD6084	Phase 2
0.6632	Remote Similarity	NPD6083	Phase 2
0.663	Remote Similarity	NPD5694	Approved
0.663	Remote Similarity	NPD6050	Approved
0.6629	Remote Similarity	NPD3618	Phase 1
0.6623	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5695	Phase 3
0.6593	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4197	Approved
0.6562	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD3667	Approved
0.6517	Remote Similarity	NPD5329	Approved
0.6471	Remote Similarity	NPD3617	Approved
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5281	Approved
0.6452	Remote Similarity	NPD5284	Approved
0.6452	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD4138	Approved
0.6444	Remote Similarity	NPD4693	Phase 3
0.6444	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5690	Phase 2
0.6444	Remote Similarity	NPD5205	Approved
0.6444	Remote Similarity	NPD4688	Approved
0.6444	Remote Similarity	NPD4689	Approved
0.6444	Remote Similarity	NPD4690	Approved
0.6444	Remote Similarity	NPD5279	Phase 3
0.6413	Remote Similarity	NPD5328	Approved
0.6413	Remote Similarity	NPD4753	Phase 2
0.6413	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD3668	Phase 3
0.6355	Remote Similarity	NPD7115	Discovery
0.6354	Remote Similarity	NPD7614	Phase 1
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD5280	Approved
0.6264	Remote Similarity	NPD4694	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5654	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4629	Approved
0.6222	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD6899	Approved
0.6211	Remote Similarity	NPD4202	Approved
0.6207	Remote Similarity	NPD4195	Approved
0.6186	Remote Similarity	NPD5222	Approved
0.6186	Remote Similarity	NPD5221	Approved
0.6186	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD6008	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.617	Remote Similarity	NPD6698	Approved
0.617	Remote Similarity	NPD46	Approved
0.6163	Remote Similarity	NPD4756	Discovery
0.6162	Remote Similarity	NPD6404	Discontinued
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD6052	Approved
0.6125	Remote Similarity	NPD7331	Phase 2
0.6122	Remote Similarity	NPD5173	Approved
0.6122	Remote Similarity	NPD5959	Approved
0.6117	Remote Similarity	NPD5701	Approved
0.6117	Remote Similarity	NPD6614	Approved
0.6117	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4788	Approved
0.6105	Remote Similarity	NPD7637	Suspended
0.6095	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD7290	Approved
0.6095	Remote Similarity	NPD6883	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.604	Remote Similarity	NPD7632	Discontinued
0.604	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD6617	Approved
0.6038	Remote Similarity	NPD8130	Phase 1
0.6038	Remote Similarity	NPD6847	Approved
0.6038	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD6649	Approved
0.6038	Remote Similarity	NPD6869	Approved
0.602	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4096	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5981	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD8297	Approved
0.5978	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6927	Phase 3
0.596	Remote Similarity	NPD3495	Discontinued
0.596	Remote Similarity	NPD4755	Approved
0.5955	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5223	Approved
0.5938	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD5362	Discontinued
0.5926	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD5909	Discontinued
0.5922	Remote Similarity	NPD5141	Approved
0.5895	Remote Similarity	NPD1695	Approved
0.5888	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5225	Approved
0.5882	Remote Similarity	NPD5224	Approved
0.5882	Remote Similarity	NPD5226	Approved
0.5882	Remote Similarity	NPD4633	Approved
0.5876	Remote Similarity	NPD5779	Approved
0.5876	Remote Similarity	NPD5778	Approved
0.5842	Remote Similarity	NPD4700	Approved
0.5825	Remote Similarity	NPD5175	Approved
0.5825	Remote Similarity	NPD5174	Approved
0.5824	Remote Similarity	NPD4270	Approved
0.5824	Remote Similarity	NPD4269	Approved
0.5818	Remote Similarity	NPD6868	Approved
0.5818	Remote Similarity	NPD6274	Approved
0.581	Remote Similarity	NPD6412	Phase 2
0.5806	Remote Similarity	NPD1696	Phase 3
0.5802	Remote Similarity	NPD7341	Phase 2
0.5794	Remote Similarity	NPD6371	Approved
0.5789	Remote Similarity	NPD4518	Approved
0.578	Remote Similarity	NPD6858	Approved
0.578	Remote Similarity	NPD7094	Approved
0.5778	Remote Similarity	NPD4252	Approved
0.5773	Remote Similarity	NPD8034	Phase 2
0.5773	Remote Similarity	NPD8035	Phase 2
0.5766	Remote Similarity	NPD6317	Approved
0.5766	Remote Similarity	NPD6009	Approved
0.5765	Remote Similarity	NPD5777	Approved
0.5761	Remote Similarity	NPD7154	Phase 3
0.5745	Remote Similarity	NPD5786	Approved
0.5732	Remote Similarity	NPD4224	Phase 2

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