NPASS Compound

Structure

CID219162 OpenBabel06191716012D 27 31 0 0 1 0 0 0 0 0999 V2000 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 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 0.8660 -3.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -0.0000 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 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 -2.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 22 1 0 0 0 0 12 20 2 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.18
Volume:	382.494
LogP:	4.481
LogD:	3.607
LogS:	-4.423
# Rotatable Bonds:	3
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	2.868
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	2.6452878955751657e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.908
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.143

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	80.9333267211914%
Volume Distribution (VD):	1.572
Pgp-substrate:	5.024379730224609%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.94
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	10.256
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.87
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.95
Carcinogencity:	0.25
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC219162

Natural Product ID:	NPC219162
*Common Name:**	(+/-)-Deoxytylophorinine
IUPAC Name:	3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
Synonyms:	(+/-)-Deoxypergularinine
Standard InCHIKey:	RFPUTOSCASFEEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H25NO3/c1-25-15-6-7-16-17-9-14-5-4-8-24(14)13-21(17)20-12-23(27-3)22(26-2)11-19(20)18(16)10-15/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3
SMILES:	COc1ccc2c3CC4CCCN4Cc3c3cc(c(cc3c2c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497756
PubChem CID:	6426880
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO7304	Ficus hispida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7304	Ficus hispida	Species	Moraceae	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
EC50	5
Others	7

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	0.011	ug.mL-1	PMID[573266]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	0.043	ug.mL-1	PMID[573266]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.023	ug.mL-1	PMID[573266]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	0.016	ug.mL-1	PMID[573266]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	26.1	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	67.4	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	60.0	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	<	25.0	ug.mL-1	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	79.2	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	65.0	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	66.7	%	PMID[573267]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	75.0	%	PMID[573267]

☑ 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 NPC219162 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	365
0.1-0.2	1626
0.2-0.3	7556
0.3-0.4	10062
0.4-0.5	7359
0.5-0.6	11921
0.6-0.7	2942
0.7-0.8	619
0.8-0.85	172
0.85-0.9	56
0.9-0.95	11
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC253883
0.9857	High Similarity	NPC95075
0.9857	High Similarity	NPC90844
0.9787	High Similarity	NPC130941
0.958	High Similarity	NPC92541
0.9521	High Similarity	NPC244112
0.9517	High Similarity	NPC26601
0.9441	High Similarity	NPC144863
0.9388	High Similarity	NPC76079
0.9324	High Similarity	NPC186063
0.9272	High Similarity	NPC233650
0.9211	High Similarity	NPC134858
0.9184	High Similarity	NPC81733
0.9184	High Similarity	NPC326316
0.9091	High Similarity	NPC210140
0.9091	High Similarity	NPC150879
0.9085	High Similarity	NPC314682
0.9021	High Similarity	NPC188163
0.9021	High Similarity	NPC474915
0.9021	High Similarity	NPC328750
0.9021	High Similarity	NPC213206
0.9013	High Similarity	NPC306902
0.9013	High Similarity	NPC232924
0.9013	High Similarity	NPC477559
0.9013	High Similarity	NPC266753
0.9013	High Similarity	NPC160298
0.8897	High Similarity	NPC476567
0.8897	High Similarity	NPC136860
0.8897	High Similarity	NPC128019
0.8889	High Similarity	NPC470925
0.8882	High Similarity	NPC476572
0.8874	High Similarity	NPC325871
0.8874	High Similarity	NPC99659
0.8851	High Similarity	NPC475959
0.8839	High Similarity	NPC225774
0.8824	High Similarity	NPC477080
0.8816	High Similarity	NPC170503
0.8816	High Similarity	NPC126519
0.8816	High Similarity	NPC203784
0.8784	High Similarity	NPC106295
0.8784	High Similarity	NPC16107
0.8784	High Similarity	NPC51957
0.8784	High Similarity	NPC210437
0.8784	High Similarity	NPC476144
0.8782	High Similarity	NPC219341
0.8782	High Similarity	NPC24264
0.8782	High Similarity	NPC476432
0.8776	High Similarity	NPC185838
0.8776	High Similarity	NPC145304
0.8766	High Similarity	NPC166014
0.8766	High Similarity	NPC27410
0.8726	High Similarity	NPC298979
0.8726	High Similarity	NPC247389
0.8725	High Similarity	NPC7467
0.8718	High Similarity	NPC16805
0.8718	High Similarity	NPC167546
0.8718	High Similarity	NPC302527
0.871	High Similarity	NPC60186
0.8671	High Similarity	NPC241055
0.8671	High Similarity	NPC11147
0.8667	High Similarity	NPC44869
0.8662	High Similarity	NPC86144
0.8662	High Similarity	NPC304659
0.8658	High Similarity	NPC321505
0.8658	High Similarity	NPC179825
0.8658	High Similarity	NPC191376
0.8658	High Similarity	NPC476151
0.8627	High Similarity	NPC216459
0.8627	High Similarity	NPC138487
0.8627	High Similarity	NPC41178
0.8618	High Similarity	NPC210148
0.8618	High Similarity	NPC233029
0.8608	High Similarity	NPC210918
0.86	High Similarity	NPC476571
0.86	High Similarity	NPC24233
0.86	High Similarity	NPC147390
0.86	High Similarity	NPC246587
0.86	High Similarity	NPC428
0.86	High Similarity	NPC135538
0.8599	High Similarity	NPC169743
0.8599	High Similarity	NPC168409
0.8592	High Similarity	NPC118419
0.8582	High Similarity	NPC160193
0.8571	High Similarity	NPC146288
0.8571	High Similarity	NPC247639
0.8571	High Similarity	NPC25084
0.8543	High Similarity	NPC211296
0.8543	High Similarity	NPC103379
0.8543	High Similarity	NPC477565
0.8535	High Similarity	NPC324144
0.8535	High Similarity	NPC189470
0.8523	High Similarity	NPC130926
0.8519	High Similarity	NPC287588
0.8506	High Similarity	NPC123323
0.8491	Intermediate Similarity	NPC474931
0.8491	Intermediate Similarity	NPC306555
0.8491	Intermediate Similarity	NPC145832
0.8491	Intermediate Similarity	NPC158376
0.8491	Intermediate Similarity	NPC12053
0.8491	Intermediate Similarity	NPC81218
0.8491	Intermediate Similarity	NPC117188
0.8491	Intermediate Similarity	NPC205421
0.8487	Intermediate Similarity	NPC97221
0.8487	Intermediate Similarity	NPC151895
0.8487	Intermediate Similarity	NPC192768
0.8487	Intermediate Similarity	NPC88249
0.8487	Intermediate Similarity	NPC220858
0.8481	Intermediate Similarity	NPC13504
0.8481	Intermediate Similarity	NPC306843
0.8481	Intermediate Similarity	NPC136508
0.8481	Intermediate Similarity	NPC196447
0.8481	Intermediate Similarity	NPC253043
0.8481	Intermediate Similarity	NPC96603
0.8481	Intermediate Similarity	NPC212794
0.8481	Intermediate Similarity	NPC477563
0.8481	Intermediate Similarity	NPC78222
0.8452	Intermediate Similarity	NPC234392
0.8452	Intermediate Similarity	NPC31311
0.8452	Intermediate Similarity	NPC477133
0.8452	Intermediate Similarity	NPC477132
0.8447	Intermediate Similarity	NPC19520
0.8447	Intermediate Similarity	NPC149090
0.844	Intermediate Similarity	NPC172403
0.8431	Intermediate Similarity	NPC476568
0.8428	Intermediate Similarity	NPC476573
0.8428	Intermediate Similarity	NPC35627
0.8428	Intermediate Similarity	NPC81247
0.8421	Intermediate Similarity	NPC60538
0.8421	Intermediate Similarity	NPC207824
0.8418	Intermediate Similarity	NPC1229
0.8395	Intermediate Similarity	NPC285941
0.8387	Intermediate Similarity	NPC295691
0.8387	Intermediate Similarity	NPC184026
0.8387	Intermediate Similarity	NPC172765
0.8387	Intermediate Similarity	NPC78733
0.8387	Intermediate Similarity	NPC5238
0.8387	Intermediate Similarity	NPC2413
0.8387	Intermediate Similarity	NPC39701
0.8387	Intermediate Similarity	NPC204828
0.8387	Intermediate Similarity	NPC110416
0.8387	Intermediate Similarity	NPC189266
0.8387	Intermediate Similarity	NPC93593
0.8387	Intermediate Similarity	NPC278799
0.8387	Intermediate Similarity	NPC127674
0.8387	Intermediate Similarity	NPC276588
0.8387	Intermediate Similarity	NPC193949
0.8387	Intermediate Similarity	NPC54379
0.8387	Intermediate Similarity	NPC249797
0.8387	Intermediate Similarity	NPC469817
0.8387	Intermediate Similarity	NPC207757
0.8385	Intermediate Similarity	NPC6152
0.8377	Intermediate Similarity	NPC470924
0.8364	Intermediate Similarity	NPC179704
0.8356	Intermediate Similarity	NPC7018
0.8354	Intermediate Similarity	NPC114364
0.8354	Intermediate Similarity	NPC320223
0.8344	Intermediate Similarity	NPC199465
0.8344	Intermediate Similarity	NPC221864
0.8344	Intermediate Similarity	NPC128560
0.8344	Intermediate Similarity	NPC229166
0.8344	Intermediate Similarity	NPC111485
0.8333	Intermediate Similarity	NPC147091
0.8312	Intermediate Similarity	NPC277669
0.8312	Intermediate Similarity	NPC76213
0.8303	Intermediate Similarity	NPC126284
0.8302	Intermediate Similarity	NPC475393
0.8299	Intermediate Similarity	NPC193528
0.8299	Intermediate Similarity	NPC253429
0.8291	Intermediate Similarity	NPC205255
0.8291	Intermediate Similarity	NPC235143
0.8291	Intermediate Similarity	NPC230956
0.8291	Intermediate Similarity	NPC119649
0.8291	Intermediate Similarity	NPC271388
0.828	Intermediate Similarity	NPC79328
0.8272	Intermediate Similarity	NPC118274
0.8272	Intermediate Similarity	NPC152212
0.8272	Intermediate Similarity	NPC168753
0.8269	Intermediate Similarity	NPC80129
0.8269	Intermediate Similarity	NPC187022
0.8261	Intermediate Similarity	NPC204947
0.8258	Intermediate Similarity	NPC148898
0.825	Intermediate Similarity	NPC232514
0.825	Intermediate Similarity	NPC238530
0.825	Intermediate Similarity	NPC76116
0.825	Intermediate Similarity	NPC276944
0.8247	Intermediate Similarity	NPC274026
0.8239	Intermediate Similarity	NPC79402
0.8239	Intermediate Similarity	NPC80759
0.8228	Intermediate Similarity	NPC7393
0.8228	Intermediate Similarity	NPC118804
0.8221	Intermediate Similarity	NPC239775
0.8217	Intermediate Similarity	NPC323443
0.8217	Intermediate Similarity	NPC180756
0.8205	Intermediate Similarity	NPC2295
0.8205	Intermediate Similarity	NPC477564
0.8204	Intermediate Similarity	NPC248642
0.8204	Intermediate Similarity	NPC249405
0.8199	Intermediate Similarity	NPC256012
0.8199	Intermediate Similarity	NPC42549
0.8199	Intermediate Similarity	NPC317272

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 NPC219162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	757
0.2-0.3	857
0.3-0.4	1774
0.4-0.5	2784
0.5-0.6	1919
0.6-0.7	678
0.7-0.8	145
0.8-0.85	18
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD4664	Clinical (unspecified phase)
0.8784	High Similarity	NPD4584	Approved
0.8535	High Similarity	NPD7201	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD4017	Approved
0.8333	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7298	Approved
0.8264	Intermediate Similarity	NPD5718	Phase 2
0.8217	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3641	Approved
0.8182	Intermediate Similarity	NPD6030	Approved
0.8182	Intermediate Similarity	NPD6031	Approved
0.8182	Intermediate Similarity	NPD3640	Phase 3
0.8182	Intermediate Similarity	NPD3639	Approved
0.8176	Intermediate Similarity	NPD7833	Phase 2
0.8176	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7831	Phase 2
0.8176	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD3109	Approved
0.8151	Intermediate Similarity	NPD3110	Approved
0.8113	Intermediate Similarity	NPD6788	Approved
0.8105	Intermediate Similarity	NPD2420	Approved
0.8105	Intermediate Similarity	NPD2421	Approved
0.8092	Intermediate Similarity	NPD5241	Discontinued
0.8025	Intermediate Similarity	NPD7802	Discontinued
0.8014	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7400	Phase 3
0.8	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8099	Discontinued
0.8	Intermediate Similarity	NPD8252	Approved
0.8	Intermediate Similarity	NPD8251	Approved
0.7975	Intermediate Similarity	NPD4773	Phase 2
0.7975	Intermediate Similarity	NPD3051	Approved
0.7975	Intermediate Similarity	NPD4772	Phase 2
0.7959	Intermediate Similarity	NPD4475	Approved
0.7959	Intermediate Similarity	NPD4474	Approved
0.7952	Intermediate Similarity	NPD8156	Discontinued
0.7922	Intermediate Similarity	NPD3845	Phase 1
0.7888	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD2898	Approved
0.7871	Intermediate Similarity	NPD3124	Discontinued
0.7867	Intermediate Similarity	NPD6895	Approved
0.7867	Intermediate Similarity	NPD6896	Approved
0.7866	Intermediate Similarity	NPD4166	Phase 2
0.7848	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5978	Approved
0.7826	Intermediate Similarity	NPD5977	Approved
0.7818	Intermediate Similarity	NPD2970	Approved
0.7818	Intermediate Similarity	NPD2969	Approved
0.7771	Intermediate Similarity	NPD4481	Phase 3
0.7771	Intermediate Similarity	NPD2489	Approved
0.7771	Intermediate Similarity	NPD27	Approved
0.7758	Intermediate Similarity	NPD4010	Discontinued
0.7756	Intermediate Similarity	NPD7598	Phase 2
0.7725	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8054	Approved
0.7674	Intermediate Similarity	NPD8053	Approved
0.7662	Intermediate Similarity	NPD7037	Approved
0.7651	Intermediate Similarity	NPD6071	Discontinued
0.7647	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2563	Approved
0.7607	Intermediate Similarity	NPD2560	Approved
0.7603	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6107	Approved
0.758	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5754	Discontinued
0.7564	Intermediate Similarity	NPD6748	Discontinued
0.7543	Intermediate Similarity	NPD7291	Discontinued
0.7534	Intermediate Similarity	NPD1669	Approved
0.7533	Intermediate Similarity	NPD7294	Phase 1
0.7531	Intermediate Similarity	NPD7110	Phase 1
0.7531	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2971	Approved
0.7514	Intermediate Similarity	NPD2968	Approved
0.7514	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6687	Approved
0.75	Intermediate Similarity	NPD4236	Phase 3
0.75	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD5976	Discontinued
0.75	Intermediate Similarity	NPD6688	Approved
0.7483	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7124	Phase 2
0.7457	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6331	Phase 2
0.7452	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7906	Approved
0.7442	Intermediate Similarity	NPD6297	Approved
0.7436	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4578	Approved
0.7414	Intermediate Similarity	NPD4577	Approved
0.7391	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4727	Phase 1
0.7389	Intermediate Similarity	NPD5177	Phase 3
0.7383	Intermediate Similarity	NPD7905	Discontinued
0.7378	Intermediate Similarity	NPD5720	Discontinued
0.7375	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1424	Approved
0.7351	Intermediate Similarity	NPD5156	Approved
0.7351	Intermediate Similarity	NPD5155	Approved
0.7338	Intermediate Similarity	NPD2492	Phase 1
0.7337	Intermediate Similarity	NPD6747	Phase 1
0.733	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5312	Approved
0.7326	Intermediate Similarity	NPD5313	Approved
0.7315	Intermediate Similarity	NPD4098	Discontinued
0.7314	Intermediate Similarity	NPD7310	Approved
0.7314	Intermediate Similarity	NPD7312	Approved
0.7314	Intermediate Similarity	NPD7311	Approved
0.7314	Intermediate Similarity	NPD7313	Approved
0.7296	Intermediate Similarity	NPD3301	Approved
0.7293	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4663	Approved
0.7285	Intermediate Similarity	NPD3595	Approved
0.7285	Intermediate Similarity	NPD2606	Approved
0.7285	Intermediate Similarity	NPD3594	Approved
0.7285	Intermediate Similarity	NPD2605	Approved
0.7284	Intermediate Similarity	NPD1914	Approved
0.7283	Intermediate Similarity	NPD7479	Phase 2
0.7283	Intermediate Similarity	NPD3920	Phase 2
0.7278	Intermediate Similarity	NPD3060	Approved
0.7278	Intermediate Similarity	NPD4162	Approved
0.7273	Intermediate Similarity	NPD6853	Approved
0.7273	Intermediate Similarity	NPD7309	Approved
0.7273	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6851	Approved
0.7267	Intermediate Similarity	NPD7020	Approved
0.7267	Intermediate Similarity	NPD7018	Phase 2
0.7267	Intermediate Similarity	NPD7019	Approved
0.7263	Intermediate Similarity	NPD2490	Approved
0.7263	Intermediate Similarity	NPD2488	Approved
0.726	Intermediate Similarity	NPD2667	Approved
0.726	Intermediate Similarity	NPD2668	Approved
0.7256	Intermediate Similarity	NPD6876	Approved
0.7256	Intermediate Similarity	NPD6875	Approved
0.7255	Intermediate Similarity	NPD2674	Phase 3
0.7254	Intermediate Similarity	NPD5283	Phase 1
0.7251	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4210	Discontinued
0.7233	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6090	Discontinued
0.7222	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3635	Approved
0.7219	Intermediate Similarity	NPD3637	Approved
0.7219	Intermediate Similarity	NPD6037	Discontinued
0.7219	Intermediate Similarity	NPD3636	Approved
0.7216	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7280	Phase 3
0.7216	Intermediate Similarity	NPD7281	Phase 3
0.7212	Intermediate Similarity	NPD7438	Suspended
0.7202	Intermediate Similarity	NPD4055	Discovery
0.7202	Intermediate Similarity	NPD5604	Discontinued
0.7192	Intermediate Similarity	NPD4093	Discontinued
0.7179	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7427	Discontinued
0.7175	Intermediate Similarity	NPD6618	Phase 2
0.7174	Intermediate Similarity	NPD8095	Phase 1
0.7158	Intermediate Similarity	NPD5564	Approved
0.7158	Intermediate Similarity	NPD7034	Discontinued
0.7152	Intermediate Similarity	NPD7247	Discontinued
0.7143	Intermediate Similarity	NPD4859	Phase 1
0.7143	Intermediate Similarity	NPD3531	Approved
0.7143	Intermediate Similarity	NPD3530	Approved
0.7143	Intermediate Similarity	NPD3532	Approved
0.7134	Intermediate Similarity	NPD1753	Discontinued
0.7127	Intermediate Similarity	NPD3921	Approved
0.7127	Intermediate Similarity	NPD3923	Approved
0.7127	Intermediate Similarity	NPD3924	Approved
0.7127	Intermediate Similarity	NPD3922	Approved
0.7126	Intermediate Similarity	NPD2977	Approved
0.7126	Intermediate Similarity	NPD2978	Approved
0.7126	Intermediate Similarity	NPD5772	Approved
0.7126	Intermediate Similarity	NPD4873	Discontinued
0.7126	Intermediate Similarity	NPD5773	Approved
0.7125	Intermediate Similarity	NPD7466	Approved
0.712	Intermediate Similarity	NPD4420	Approved
0.7118	Intermediate Similarity	NPD5677	Discontinued
0.7114	Intermediate Similarity	NPD2233	Approved
0.7114	Intermediate Similarity	NPD2232	Approved
0.7114	Intermediate Similarity	NPD2230	Approved
0.711	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5938	Phase 3
0.7108	Intermediate Similarity	NPD6873	Phase 2
0.7107	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4005	Discontinued
0.7089	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5160	Discontinued
0.7078	Intermediate Similarity	NPD3144	Approved
0.7078	Intermediate Similarity	NPD5109	Approved
0.7078	Intermediate Similarity	NPD5111	Phase 2
0.7078	Intermediate Similarity	NPD5110	Phase 2
0.7078	Intermediate Similarity	NPD3145	Approved
0.7075	Intermediate Similarity	NPD2594	Approved
0.7075	Intermediate Similarity	NPD2595	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