NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	1.495
LogD:	1.69
LogS:	-2.908
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.546
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	1.9162980606779456e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.576
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.663
Plasma Protein Binding (PPB):	88.98355865478516%
Volume Distribution (VD):	1.236
Pgp-substrate:	8.816781997680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.256
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.434
CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.471
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.701
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	8.859
Half-life (T1/2):	0.51

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.11
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.696
Carcinogencity:	0.256
Eye Corrosion:	0.306
Eye Irritation:	0.369
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: NPC471465

Natural Product ID:	NPC471465
*Common Name:**	Tamaulipin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XQVSREKNQZKAKU-RDUBSVMPSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5-,10-8+/t12-,13+,14+/m0/s1
SMILES:	C/C/1=C/C[C@@H](O)/C(=C/[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251598
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	4.98	n.a.	PMID[464506]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.6	ug ml-1	PMID[464506]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	10.5	umol/L	PMID[464507]

☑ 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 NPC471465 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	156
0.1-0.2	1117
0.2-0.3	5538
0.3-0.4	15131
0.4-0.5	10793
0.5-0.6	6319
0.6-0.7	2788
0.7-0.8	693
0.8-0.85	63
0.85-0.9	54
0.9-0.95	37
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196653
0.96	High Similarity	NPC24417
0.9595	High Similarity	NPC98557
0.9595	High Similarity	NPC167881
0.9589	High Similarity	NPC116177
0.9589	High Similarity	NPC7563
0.9589	High Similarity	NPC320630
0.9474	High Similarity	NPC229825
0.9351	High Similarity	NPC473390
0.9351	High Similarity	NPC169575
0.9351	High Similarity	NPC40746
0.9351	High Similarity	NPC131669
0.9306	High Similarity	NPC58956
0.9306	High Similarity	NPC269206
0.9306	High Similarity	NPC295633
0.9231	High Similarity	NPC158756
0.9231	High Similarity	NPC114979
0.9231	High Similarity	NPC191476
0.9231	High Similarity	NPC141193
0.9231	High Similarity	NPC96259
0.9231	High Similarity	NPC476804
0.92	High Similarity	NPC108816
0.92	High Similarity	NPC267231
0.92	High Similarity	NPC93763
0.9114	High Similarity	NPC470755
0.9114	High Similarity	NPC255307
0.9103	High Similarity	NPC59097
0.9091	High Similarity	NPC52861
0.9079	High Similarity	NPC89128
0.9	High Similarity	NPC475461
0.9	High Similarity	NPC305475
0.9	High Similarity	NPC469910
0.8933	High Similarity	NPC235906
0.8933	High Similarity	NPC68819
0.8904	High Similarity	NPC163003
0.8831	High Similarity	NPC470239
0.8831	High Similarity	NPC470244
0.8816	High Similarity	NPC141789
0.8816	High Similarity	NPC476028
0.8816	High Similarity	NPC171204
0.88	High Similarity	NPC155587
0.878	High Similarity	NPC476805
0.878	High Similarity	NPC475819
0.878	High Similarity	NPC473715
0.878	High Similarity	NPC476803
0.8675	High Similarity	NPC474032
0.8667	High Similarity	NPC140287
0.8667	High Similarity	NPC476355
0.8649	High Similarity	NPC129665
0.8642	High Similarity	NPC165162
0.8642	High Similarity	NPC21469
0.8625	High Similarity	NPC116543
0.8625	High Similarity	NPC250315
0.859	High Similarity	NPC270126
0.8571	High Similarity	NPC474232
0.8571	High Similarity	NPC475855
0.8571	High Similarity	NPC469368
0.8537	High Similarity	NPC150755
0.8481	Intermediate Similarity	NPC281132
0.8471	Intermediate Similarity	NPC473321
0.8442	Intermediate Similarity	NPC123360
0.8375	Intermediate Similarity	NPC325031
0.8372	Intermediate Similarity	NPC125674
0.8372	Intermediate Similarity	NPC475838
0.8372	Intermediate Similarity	NPC273579
0.8372	Intermediate Similarity	NPC228451
0.8372	Intermediate Similarity	NPC288240
0.8372	Intermediate Similarity	NPC295204
0.8372	Intermediate Similarity	NPC162205
0.8353	Intermediate Similarity	NPC144133
0.8353	Intermediate Similarity	NPC179394
0.8353	Intermediate Similarity	NPC473619
0.8333	Intermediate Similarity	NPC65603
0.8333	Intermediate Similarity	NPC187568
0.8333	Intermediate Similarity	NPC41780
0.8333	Intermediate Similarity	NPC97516
0.8312	Intermediate Similarity	NPC138408
0.8312	Intermediate Similarity	NPC193351
0.8312	Intermediate Similarity	NPC226669
0.8276	Intermediate Similarity	NPC303942
0.8276	Intermediate Similarity	NPC474247
0.8276	Intermediate Similarity	NPC57405
0.8272	Intermediate Similarity	NPC89555
0.8235	Intermediate Similarity	NPC295312
0.8235	Intermediate Similarity	NPC268298
0.8214	Intermediate Similarity	NPC160138
0.8193	Intermediate Similarity	NPC261380
0.8182	Intermediate Similarity	NPC471142
0.8182	Intermediate Similarity	NPC477922
0.8182	Intermediate Similarity	NPC114727
0.8182	Intermediate Similarity	NPC476590
0.8161	Intermediate Similarity	NPC475302
0.814	Intermediate Similarity	NPC129419
0.8118	Intermediate Similarity	NPC136879
0.8108	Intermediate Similarity	NPC194871
0.8101	Intermediate Similarity	NPC476794
0.8101	Intermediate Similarity	NPC470240
0.8101	Intermediate Similarity	NPC474760
0.809	Intermediate Similarity	NPC279621
0.809	Intermediate Similarity	NPC477921
0.809	Intermediate Similarity	NPC230800
0.8049	Intermediate Similarity	NPC85772
0.8026	Intermediate Similarity	NPC67183
0.8023	Intermediate Similarity	NPC206001
0.8023	Intermediate Similarity	NPC218927
0.8	Intermediate Similarity	NPC470256
0.7955	Intermediate Similarity	NPC469692
0.7955	Intermediate Similarity	NPC475912
0.7955	Intermediate Similarity	NPC469645
0.7949	Intermediate Similarity	NPC472966
0.7949	Intermediate Similarity	NPC48641
0.7931	Intermediate Similarity	NPC106510
0.7931	Intermediate Similarity	NPC476004
0.7931	Intermediate Similarity	NPC474761
0.7931	Intermediate Similarity	NPC71533
0.7927	Intermediate Similarity	NPC301477
0.7927	Intermediate Similarity	NPC470241
0.7927	Intermediate Similarity	NPC25684
0.7927	Intermediate Similarity	NPC281949
0.7927	Intermediate Similarity	NPC141810
0.7922	Intermediate Similarity	NPC472254
0.7907	Intermediate Similarity	NPC202672
0.7907	Intermediate Similarity	NPC477302
0.7901	Intermediate Similarity	NPC617
0.7901	Intermediate Similarity	NPC472965
0.7901	Intermediate Similarity	NPC182550
0.7901	Intermediate Similarity	NPC475210
0.7901	Intermediate Similarity	NPC178277
0.7901	Intermediate Similarity	NPC264227
0.7901	Intermediate Similarity	NPC63649
0.7889	Intermediate Similarity	NPC306041
0.7889	Intermediate Similarity	NPC473859
0.7882	Intermediate Similarity	NPC50637
0.7882	Intermediate Similarity	NPC261721
0.7875	Intermediate Similarity	NPC57744
0.7865	Intermediate Similarity	NPC81386
0.7865	Intermediate Similarity	NPC474035
0.7865	Intermediate Similarity	NPC121825
0.7857	Intermediate Similarity	NPC472958
0.7857	Intermediate Similarity	NPC156485
0.7857	Intermediate Similarity	NPC472957
0.7857	Intermediate Similarity	NPC70424
0.7857	Intermediate Similarity	NPC243618
0.7857	Intermediate Similarity	NPC82297
0.7848	Intermediate Similarity	NPC329852
0.7841	Intermediate Similarity	NPC111114
0.7841	Intermediate Similarity	NPC300312
0.7841	Intermediate Similarity	NPC261607
0.7841	Intermediate Similarity	NPC30515
0.7831	Intermediate Similarity	NPC474291
0.7831	Intermediate Similarity	NPC173609
0.7831	Intermediate Similarity	NPC474252
0.7826	Intermediate Similarity	NPC288876
0.7821	Intermediate Similarity	NPC275098
0.7805	Intermediate Similarity	NPC302426
0.7805	Intermediate Similarity	NPC276356
0.7792	Intermediate Similarity	NPC4299
0.7791	Intermediate Similarity	NPC237540
0.7791	Intermediate Similarity	NPC266957
0.7791	Intermediate Similarity	NPC72513
0.7791	Intermediate Similarity	NPC312561
0.7778	Intermediate Similarity	NPC128276
0.7778	Intermediate Similarity	NPC14961
0.7778	Intermediate Similarity	NPC304886
0.7778	Intermediate Similarity	NPC36954
0.7778	Intermediate Similarity	NPC270013
0.7778	Intermediate Similarity	NPC471141
0.7778	Intermediate Similarity	NPC475659
0.7778	Intermediate Similarity	NPC472960
0.7765	Intermediate Similarity	NPC215364
0.7765	Intermediate Similarity	NPC319795
0.7765	Intermediate Similarity	NPC38468
0.7765	Intermediate Similarity	NPC50362
0.7753	Intermediate Similarity	NPC81419
0.7753	Intermediate Similarity	NPC179746
0.7738	Intermediate Similarity	NPC318468
0.7738	Intermediate Similarity	NPC474703
0.7727	Intermediate Similarity	NPC158488
0.7727	Intermediate Similarity	NPC37607
0.7727	Intermediate Similarity	NPC51004
0.7727	Intermediate Similarity	NPC301969
0.7717	Intermediate Similarity	NPC471144
0.7717	Intermediate Similarity	NPC473326
0.7711	Intermediate Similarity	NPC471325
0.7701	Intermediate Similarity	NPC287089
0.7701	Intermediate Similarity	NPC277771
0.7701	Intermediate Similarity	NPC91248
0.7692	Intermediate Similarity	NPC477087
0.7692	Intermediate Similarity	NPC477086
0.7692	Intermediate Similarity	NPC476315
0.7683	Intermediate Similarity	NPC19841
0.7674	Intermediate Similarity	NPC67493
0.7674	Intermediate Similarity	NPC469483
0.7674	Intermediate Similarity	NPC284902
0.7667	Intermediate Similarity	NPC262133
0.7667	Intermediate Similarity	NPC470013
0.7667	Intermediate Similarity	NPC323008
0.7667	Intermediate Similarity	NPC167219
0.7667	Intermediate Similarity	NPC474338
0.7667	Intermediate Similarity	NPC470010

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 NPC471465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1672
0.2-0.3	3906
0.3-0.4	2392
0.4-0.5	687
0.5-0.6	286
0.6-0.7	45
0.7-0.8	17
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
0.7765	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7154	Phase 3
0.7528	Intermediate Similarity	NPD5785	Approved
0.7391	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5363	Approved
0.7326	Intermediate Similarity	NPD5362	Discontinued
0.7209	Intermediate Similarity	NPD4269	Approved
0.7209	Intermediate Similarity	NPD4270	Approved
0.7176	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4252	Approved
0.7159	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7079	Intermediate Similarity	NPD5786	Approved
0.7033	Intermediate Similarity	NPD1695	Approved
0.6979	Remote Similarity	NPD4225	Approved
0.6966	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4271	Approved
0.6941	Remote Similarity	NPD4268	Approved
0.6897	Remote Similarity	NPD5369	Approved
0.6889	Remote Similarity	NPD4249	Approved
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4251	Approved
0.6813	Remote Similarity	NPD4250	Approved
0.6782	Remote Similarity	NPD4820	Approved
0.6782	Remote Similarity	NPD4821	Approved
0.6782	Remote Similarity	NPD4819	Approved
0.6782	Remote Similarity	NPD4822	Approved
0.6742	Remote Similarity	NPD5332	Approved
0.6742	Remote Similarity	NPD5331	Approved
0.6709	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4790	Discontinued
0.6702	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6371	Approved
0.6633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5778	Approved
0.6632	Remote Similarity	NPD5779	Approved
0.6629	Remote Similarity	NPD6435	Approved
0.6629	Remote Similarity	NPD5209	Approved
0.6628	Remote Similarity	NPD4756	Discovery
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7838	Discovery
0.6588	Remote Similarity	NPD8039	Approved
0.6526	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7839	Suspended
0.6415	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5368	Approved
0.64	Remote Similarity	NPD7640	Approved
0.64	Remote Similarity	NPD7639	Approved
0.6375	Remote Similarity	NPD3197	Phase 1
0.6341	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7638	Approved
0.6289	Remote Similarity	NPD6399	Phase 3
0.6286	Remote Similarity	NPD6686	Approved
0.6273	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD7637	Suspended
0.6186	Remote Similarity	NPD6411	Approved
0.6184	Remote Similarity	NPD342	Phase 1
0.617	Remote Similarity	NPD6422	Discontinued
0.6133	Remote Similarity	NPD3172	Approved
0.6125	Remote Similarity	NPD368	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.6081	Remote Similarity	NPD6927	Phase 3
0.6061	Remote Similarity	NPD5282	Discontinued
0.6058	Remote Similarity	NPD6647	Phase 2
0.6055	Remote Similarity	NPD6053	Discontinued
0.6053	Remote Similarity	NPD3196	Approved
0.6053	Remote Similarity	NPD3194	Approved
0.6053	Remote Similarity	NPD3195	Phase 2
0.6053	Remote Similarity	NPD4266	Approved
0.6024	Remote Similarity	NPD7331	Phase 2
0.6022	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5957	Remote Similarity	NPD3666	Approved
0.5957	Remote Similarity	NPD3133	Approved
0.5957	Remote Similarity	NPD3665	Phase 1
0.5957	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8516	Approved
0.5913	Remote Similarity	NPD8517	Approved
0.5913	Remote Similarity	NPD8515	Approved
0.5913	Remote Similarity	NPD8513	Phase 3
0.59	Remote Similarity	NPD7748	Approved
0.5895	Remote Similarity	NPD1696	Phase 3
0.5882	Remote Similarity	NPD6084	Phase 2
0.5882	Remote Similarity	NPD6083	Phase 2
0.5882	Remote Similarity	NPD7902	Approved
0.5876	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6903	Approved
0.5859	Remote Similarity	NPD7515	Phase 2
0.5854	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5695	Phase 3
0.5833	Remote Similarity	NPD3704	Approved
0.5833	Remote Similarity	NPD5279	Phase 3
0.5825	Remote Similarity	NPD5696	Approved
0.5818	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD3173	Approved
0.581	Remote Similarity	NPD7632	Discontinued
0.5769	Remote Similarity	NPD6648	Approved
0.5741	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD7341	Phase 2
0.5714	Remote Similarity	NPD5737	Approved
0.5714	Remote Similarity	NPD6672	Approved
0.57	Remote Similarity	NPD5693	Phase 1
0.57	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD4695	Discontinued
0.5688	Remote Similarity	NPD6881	Approved
0.5688	Remote Similarity	NPD6899	Approved
0.5688	Remote Similarity	NPD6011	Approved
0.5679	Remote Similarity	NPD3198	Approved
0.5676	Remote Similarity	NPD6650	Approved
0.5676	Remote Similarity	NPD6649	Approved
0.5676	Remote Similarity	NPD622	Approved
0.567	Remote Similarity	NPD4519	Discontinued
0.567	Remote Similarity	NPD4623	Approved
0.5667	Remote Similarity	NPD8074	Phase 3
0.5658	Remote Similarity	NPD28	Approved
0.5658	Remote Similarity	NPD29	Approved
0.5657	Remote Similarity	NPD5328	Approved
0.5652	Remote Similarity	NPD3732	Approved
0.5648	Remote Similarity	NPD7128	Approved
0.5648	Remote Similarity	NPD6675	Approved
0.5648	Remote Similarity	NPD5739	Approved
0.5648	Remote Similarity	NPD6402	Approved
0.5647	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD9298	Approved
0.5638	Remote Similarity	NPD857	Phase 3
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6013	Approved
0.5636	Remote Similarity	NPD6012	Approved
0.5636	Remote Similarity	NPD6373	Approved
0.5636	Remote Similarity	NPD6014	Approved
0.5631	Remote Similarity	NPD4228	Discovery
0.5625	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5207	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