NPASS Compound

Structure

CID90844 OpenBabel06191715432D 27 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -5.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 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 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 -2.5981 -1.5000 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 -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 -2.5981 -2.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 1 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 19 20 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:	4.735
LogD:	3.533
LogS:	-5.515
# 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:	-5.012
MDCK Permeability:	3.4396689443383366e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.162

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	75.11013793945312%
Volume Distribution (VD):	1.479
Pgp-substrate:	8.996047019958496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.721
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.984
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.843

ADMET: Excretion

Clearance (CL):	10.274
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.55
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.954
Carcinogencity:	0.253
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC90844

Natural Product ID:	NPC90844
*Common Name:**	Hypoestestatin 1
IUPAC Name:	(13aS)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
Synonyms:	Hypoestestatin 1
Standard InCHIKey:	NCVWJDISIZHFQS-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m0/s1
SMILES:	COc1ccc2c(c1)c1cc(c(cc1c1C[C@@H]3CCCN3Cc21)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483423
PubChem CID:	12019847
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
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1
GI50	2
Others	16

Activity Type	# Activity
Cell Line	3
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.3	10'-5 ug/ml	PMID[453396]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	200.0	nM	PMID[453397]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	300.0	nM	PMID[453397]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	28.4	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	56.4	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	26.7	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	55.5	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	37.2	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Activity	=	51.1	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.5	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	60.2	%	PMID[453398]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	28.4	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	56.4	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	26.7	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	55.5	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	37.2	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	51.1	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.5	%	PMID[453399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	60.2	%	PMID[453399]

☑ 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 NPC90844 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	337
0.1-0.2	1630
0.2-0.3	7137
0.3-0.4	10491
0.4-0.5	6943
0.5-0.6	12078
0.6-0.7	3197
0.7-0.8	685
0.8-0.85	150
0.85-0.9	32
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95075
1.0	High Similarity	NPC253883
0.9857	High Similarity	NPC219162
0.965	High Similarity	NPC26601
0.9645	High Similarity	NPC130941
0.9574	High Similarity	NPC144863
0.9517	High Similarity	NPC76079
0.9441	High Similarity	NPC92541
0.9384	High Similarity	NPC244112
0.9189	High Similarity	NPC186063
0.9139	High Similarity	NPC233650
0.9079	High Similarity	NPC134858
0.9048	High Similarity	NPC326316
0.9048	High Similarity	NPC81733
0.8961	High Similarity	NPC150879
0.8961	High Similarity	NPC210140
0.8944	High Similarity	NPC314682
0.8882	High Similarity	NPC306902
0.8882	High Similarity	NPC232924
0.8882	High Similarity	NPC160298
0.8882	High Similarity	NPC477559
0.8882	High Similarity	NPC266753
0.8881	High Similarity	NPC213206
0.8881	High Similarity	NPC474915
0.8881	High Similarity	NPC328750
0.8881	High Similarity	NPC188163
0.8784	High Similarity	NPC44869
0.8759	High Similarity	NPC136860
0.8759	High Similarity	NPC128019
0.8759	High Similarity	NPC476567
0.875	High Similarity	NPC470925
0.875	High Similarity	NPC476572
0.8742	High Similarity	NPC99659
0.8742	High Similarity	NPC325871
0.8716	High Similarity	NPC475959
0.8714	High Similarity	NPC118419
0.871	High Similarity	NPC225774
0.871	High Similarity	NPC169743
0.8693	High Similarity	NPC477080
0.8684	High Similarity	NPC170503
0.8684	High Similarity	NPC126519
0.8684	High Similarity	NPC203784
0.8654	High Similarity	NPC24264
0.8654	High Similarity	NPC476432
0.8654	High Similarity	NPC219341
0.8649	High Similarity	NPC210437
0.8649	High Similarity	NPC106295
0.8649	High Similarity	NPC476144
0.8649	High Similarity	NPC16107
0.8649	High Similarity	NPC51957
0.8639	High Similarity	NPC145304
0.8639	High Similarity	NPC185838
0.8636	High Similarity	NPC27410
0.8636	High Similarity	NPC166014
0.8599	High Similarity	NPC298979
0.8599	High Similarity	NPC247389
0.8591	High Similarity	NPC7467
0.859	High Similarity	NPC167546
0.859	High Similarity	NPC302527
0.859	High Similarity	NPC16805
0.8581	High Similarity	NPC60186
0.8544	High Similarity	NPC241055
0.8535	High Similarity	NPC86144
0.8535	High Similarity	NPC304659
0.8531	High Similarity	NPC11147
0.8523	High Similarity	NPC321505
0.8523	High Similarity	NPC179825
0.8523	High Similarity	NPC476151
0.8523	High Similarity	NPC191376
0.8497	Intermediate Similarity	NPC138487
0.8497	Intermediate Similarity	NPC41178
0.8497	Intermediate Similarity	NPC216459
0.8487	Intermediate Similarity	NPC233029
0.8487	Intermediate Similarity	NPC210148
0.8481	Intermediate Similarity	NPC210918
0.8471	Intermediate Similarity	NPC168409
0.8467	Intermediate Similarity	NPC147390
0.8467	Intermediate Similarity	NPC246587
0.8467	Intermediate Similarity	NPC135538
0.8467	Intermediate Similarity	NPC428
0.8467	Intermediate Similarity	NPC476571
0.8467	Intermediate Similarity	NPC24233
0.8442	Intermediate Similarity	NPC247639
0.8442	Intermediate Similarity	NPC25084
0.8442	Intermediate Similarity	NPC146288
0.844	Intermediate Similarity	NPC160193
0.8414	Intermediate Similarity	NPC193528
0.8411	Intermediate Similarity	NPC211296
0.8411	Intermediate Similarity	NPC103379
0.8411	Intermediate Similarity	NPC477565
0.8408	Intermediate Similarity	NPC324144
0.8408	Intermediate Similarity	NPC189470
0.8395	Intermediate Similarity	NPC287588
0.8389	Intermediate Similarity	NPC130926
0.8377	Intermediate Similarity	NPC123323
0.8365	Intermediate Similarity	NPC81218
0.8365	Intermediate Similarity	NPC158376
0.8365	Intermediate Similarity	NPC12053
0.8365	Intermediate Similarity	NPC117188
0.8365	Intermediate Similarity	NPC205421
0.8365	Intermediate Similarity	NPC306555
0.8365	Intermediate Similarity	NPC145832
0.8365	Intermediate Similarity	NPC474931
0.8355	Intermediate Similarity	NPC220858
0.8355	Intermediate Similarity	NPC151895
0.8355	Intermediate Similarity	NPC192768
0.8355	Intermediate Similarity	NPC97221
0.8355	Intermediate Similarity	NPC88249
0.8354	Intermediate Similarity	NPC306843
0.8354	Intermediate Similarity	NPC196447
0.8354	Intermediate Similarity	NPC253043
0.8354	Intermediate Similarity	NPC96603
0.8354	Intermediate Similarity	NPC477563
0.8354	Intermediate Similarity	NPC212794
0.8354	Intermediate Similarity	NPC136508
0.8354	Intermediate Similarity	NPC78222
0.8354	Intermediate Similarity	NPC13504
0.8323	Intermediate Similarity	NPC19520
0.8323	Intermediate Similarity	NPC477132
0.8323	Intermediate Similarity	NPC31311
0.8323	Intermediate Similarity	NPC149090
0.8323	Intermediate Similarity	NPC477133
0.8323	Intermediate Similarity	NPC234392
0.8302	Intermediate Similarity	NPC476573
0.8302	Intermediate Similarity	NPC35627
0.8302	Intermediate Similarity	NPC81247
0.8301	Intermediate Similarity	NPC476568
0.8298	Intermediate Similarity	NPC172403
0.8291	Intermediate Similarity	NPC1229
0.8289	Intermediate Similarity	NPC60538
0.8289	Intermediate Similarity	NPC207824
0.8272	Intermediate Similarity	NPC285941
0.8264	Intermediate Similarity	NPC325568
0.8261	Intermediate Similarity	NPC6152
0.8258	Intermediate Similarity	NPC127674
0.8258	Intermediate Similarity	NPC39701
0.8258	Intermediate Similarity	NPC172765
0.8258	Intermediate Similarity	NPC78733
0.8258	Intermediate Similarity	NPC54379
0.8258	Intermediate Similarity	NPC189266
0.8258	Intermediate Similarity	NPC204828
0.8258	Intermediate Similarity	NPC193949
0.8258	Intermediate Similarity	NPC207757
0.8258	Intermediate Similarity	NPC184026
0.8258	Intermediate Similarity	NPC469817
0.8258	Intermediate Similarity	NPC2413
0.8258	Intermediate Similarity	NPC249797
0.8258	Intermediate Similarity	NPC276588
0.8258	Intermediate Similarity	NPC295691
0.8258	Intermediate Similarity	NPC110416
0.8258	Intermediate Similarity	NPC93593
0.8258	Intermediate Similarity	NPC5238
0.8258	Intermediate Similarity	NPC278799
0.8247	Intermediate Similarity	NPC470924
0.8242	Intermediate Similarity	NPC179704
0.8232	Intermediate Similarity	NPC114364
0.8232	Intermediate Similarity	NPC320223
0.8221	Intermediate Similarity	NPC199465
0.8221	Intermediate Similarity	NPC128560
0.8221	Intermediate Similarity	NPC229166
0.8219	Intermediate Similarity	NPC7018
0.8217	Intermediate Similarity	NPC111485
0.8217	Intermediate Similarity	NPC221864
0.8205	Intermediate Similarity	NPC147091
0.8182	Intermediate Similarity	NPC76213
0.8182	Intermediate Similarity	NPC126284
0.8182	Intermediate Similarity	NPC52475
0.8182	Intermediate Similarity	NPC277669
0.8176	Intermediate Similarity	NPC475393
0.8165	Intermediate Similarity	NPC119649
0.8165	Intermediate Similarity	NPC235143
0.8165	Intermediate Similarity	NPC230956
0.8165	Intermediate Similarity	NPC205255
0.8165	Intermediate Similarity	NPC271388
0.8163	Intermediate Similarity	NPC253429
0.8153	Intermediate Similarity	NPC79328
0.8148	Intermediate Similarity	NPC168753
0.8148	Intermediate Similarity	NPC118274
0.8148	Intermediate Similarity	NPC152212
0.8141	Intermediate Similarity	NPC80129
0.8141	Intermediate Similarity	NPC187022
0.8137	Intermediate Similarity	NPC204947
0.8129	Intermediate Similarity	NPC148898
0.8129	Intermediate Similarity	NPC18614
0.8125	Intermediate Similarity	NPC276944
0.8125	Intermediate Similarity	NPC76116
0.8125	Intermediate Similarity	NPC238530
0.8125	Intermediate Similarity	NPC232514
0.8117	Intermediate Similarity	NPC274026
0.8113	Intermediate Similarity	NPC80759
0.8113	Intermediate Similarity	NPC79402
0.8101	Intermediate Similarity	NPC118804
0.8101	Intermediate Similarity	NPC7393
0.8098	Intermediate Similarity	NPC239775
0.8089	Intermediate Similarity	NPC180756
0.8089	Intermediate Similarity	NPC323443
0.8084	Intermediate Similarity	NPC248642
0.8084	Intermediate Similarity	NPC249405
0.8077	Intermediate Similarity	NPC2295
0.8077	Intermediate Similarity	NPC477564

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 NPC90844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	767
0.2-0.3	839
0.3-0.4	1751
0.4-0.5	2800
0.5-0.6	1901
0.6-0.7	698
0.7-0.8	169
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD4664	Clinical (unspecified phase)
0.8649	High Similarity	NPD4584	Approved
0.8408	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD4017	Approved
0.8264	Intermediate Similarity	NPD3109	Approved
0.8264	Intermediate Similarity	NPD3110	Approved
0.82	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7298	Approved
0.8125	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5718	Phase 2
0.8089	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD4474	Approved
0.8069	Intermediate Similarity	NPD4475	Approved
0.8056	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3641	Approved
0.8052	Intermediate Similarity	NPD6031	Approved
0.8052	Intermediate Similarity	NPD3639	Approved
0.8052	Intermediate Similarity	NPD6030	Approved
0.8052	Intermediate Similarity	NPD3640	Phase 3
0.805	Intermediate Similarity	NPD7831	Phase 2
0.805	Intermediate Similarity	NPD7833	Phase 2
0.805	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6788	Approved
0.7974	Intermediate Similarity	NPD2420	Approved
0.7974	Intermediate Similarity	NPD2421	Approved
0.7961	Intermediate Similarity	NPD5241	Discontinued
0.7925	Intermediate Similarity	NPD5978	Approved
0.7925	Intermediate Similarity	NPD5977	Approved
0.7901	Intermediate Similarity	NPD7802	Discontinued
0.7888	Intermediate Similarity	NPD7400	Phase 3
0.7879	Intermediate Similarity	NPD8252	Approved
0.7879	Intermediate Similarity	NPD8251	Approved
0.7879	Intermediate Similarity	NPD8099	Discontinued
0.7862	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7598	Phase 2
0.7853	Intermediate Similarity	NPD3051	Approved
0.7848	Intermediate Similarity	NPD4773	Phase 2
0.7848	Intermediate Similarity	NPD4772	Phase 2
0.7831	Intermediate Similarity	NPD8156	Discontinued
0.7792	Intermediate Similarity	NPD3845	Phase 1
0.7764	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7037	Approved
0.7758	Intermediate Similarity	NPD2898	Approved
0.7744	Intermediate Similarity	NPD4166	Phase 2
0.7742	Intermediate Similarity	NPD3124	Discontinued
0.7738	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6896	Approved
0.7733	Intermediate Similarity	NPD6895	Approved
0.7727	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2970	Approved
0.7697	Intermediate Similarity	NPD2969	Approved
0.7667	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6748	Discontinued
0.7651	Intermediate Similarity	NPD27	Approved
0.7651	Intermediate Similarity	NPD2489	Approved
0.7651	Intermediate Similarity	NPD4481	Phase 3
0.7639	Intermediate Similarity	NPD1669	Approved
0.7636	Intermediate Similarity	NPD4010	Discontinued
0.7635	Intermediate Similarity	NPD7294	Phase 1
0.7605	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4236	Phase 3
0.7597	Intermediate Similarity	NPD4237	Approved
0.7595	Intermediate Similarity	NPD5976	Discontinued
0.7558	Intermediate Similarity	NPD8053	Approved
0.7558	Intermediate Similarity	NPD8054	Approved
0.7532	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6071	Discontinued
0.7485	Intermediate Similarity	NPD2560	Approved
0.7485	Intermediate Similarity	NPD2563	Approved
0.7484	Intermediate Similarity	NPD4727	Phase 1
0.7484	Intermediate Similarity	NPD5177	Phase 3
0.747	Intermediate Similarity	NPD6107	Approved
0.7452	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5156	Approved
0.745	Intermediate Similarity	NPD5155	Approved
0.7436	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5754	Discontinued
0.7436	Intermediate Similarity	NPD6331	Phase 2
0.7434	Intermediate Similarity	NPD2492	Phase 1
0.7429	Intermediate Similarity	NPD7291	Discontinued
0.7407	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7110	Phase 1
0.7399	Intermediate Similarity	NPD2971	Approved
0.7399	Intermediate Similarity	NPD2968	Approved
0.7399	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3301	Approved
0.7383	Intermediate Similarity	NPD3595	Approved
0.7383	Intermediate Similarity	NPD2606	Approved
0.7383	Intermediate Similarity	NPD3594	Approved
0.7383	Intermediate Similarity	NPD2605	Approved
0.7381	Intermediate Similarity	NPD6688	Approved
0.7381	Intermediate Similarity	NPD6687	Approved
0.7375	Intermediate Similarity	NPD1914	Approved
0.7365	Intermediate Similarity	NPD7018	Phase 2
0.7362	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2667	Approved
0.7361	Intermediate Similarity	NPD2668	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7351	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7124	Phase 2
0.7341	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7906	Approved
0.7326	Intermediate Similarity	NPD6297	Approved
0.7325	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3637	Approved
0.7315	Intermediate Similarity	NPD3636	Approved
0.7315	Intermediate Similarity	NPD3635	Approved
0.7312	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6090	Discontinued
0.7301	Intermediate Similarity	NPD7438	Suspended
0.7299	Intermediate Similarity	NPD4578	Approved
0.7299	Intermediate Similarity	NPD4577	Approved
0.7292	Intermediate Similarity	NPD4093	Discontinued
0.7289	Intermediate Similarity	NPD5604	Discontinued
0.7273	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7427	Discontinued
0.7256	Intermediate Similarity	NPD5720	Discontinued
0.725	Intermediate Similarity	NPD1424	Approved
0.725	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7247	Discontinued
0.7248	Intermediate Similarity	NPD7905	Discontinued
0.7237	Intermediate Similarity	NPD3530	Approved
0.7237	Intermediate Similarity	NPD3531	Approved
0.7237	Intermediate Similarity	NPD3532	Approved
0.7237	Intermediate Similarity	NPD2674	Phase 3
0.7219	Intermediate Similarity	NPD6747	Phase 1
0.7216	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7466	Approved
0.7211	Intermediate Similarity	NPD2230	Approved
0.7211	Intermediate Similarity	NPD2232	Approved
0.7211	Intermediate Similarity	NPD2233	Approved
0.7209	Intermediate Similarity	NPD5312	Approved
0.7209	Intermediate Similarity	NPD5313	Approved
0.72	Intermediate Similarity	NPD7313	Approved
0.72	Intermediate Similarity	NPD7311	Approved
0.72	Intermediate Similarity	NPD7312	Approved
0.72	Intermediate Similarity	NPD7310	Approved
0.7197	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6873	Phase 2
0.7193	Intermediate Similarity	NPD5938	Phase 3
0.7186	Intermediate Similarity	NPD4055	Discovery
0.7182	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4098	Discontinued
0.7175	Intermediate Similarity	NPD4663	Approved
0.7172	Intermediate Similarity	NPD2594	Approved
0.7172	Intermediate Similarity	NPD2595	Approved
0.7171	Intermediate Similarity	NPD5111	Phase 2
0.7171	Intermediate Similarity	NPD5110	Phase 2
0.7171	Intermediate Similarity	NPD5109	Approved
0.717	Intermediate Similarity	NPD5160	Discontinued
0.7169	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7479	Phase 2
0.7168	Intermediate Similarity	NPD3920	Phase 2
0.7162	Intermediate Similarity	NPD1421	Approved
0.7162	Intermediate Similarity	NPD1420	Approved
0.7161	Intermediate Similarity	NPD6111	Discontinued
0.7159	Intermediate Similarity	NPD6851	Approved
0.7159	Intermediate Similarity	NPD7309	Approved
0.7159	Intermediate Similarity	NPD6853	Approved
0.7152	Intermediate Similarity	NPD3060	Approved
0.7152	Intermediate Similarity	NPD4162	Approved
0.7151	Intermediate Similarity	NPD2488	Approved
0.7151	Intermediate Similarity	NPD2490	Approved
0.7143	Intermediate Similarity	NPD7019	Approved
0.7143	Intermediate Similarity	NPD7020	Approved
0.7134	Intermediate Similarity	NPD6876	Approved
0.7134	Intermediate Similarity	NPD6875	Approved
0.7133	Intermediate Similarity	NPD6584	Phase 3
0.7125	Intermediate Similarity	NPD2120	Phase 2
0.7125	Intermediate Similarity	NPD6066	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4210	Discontinued
0.7115	Intermediate Similarity	NPD4108	Discontinued
0.7108	Intermediate Similarity	NPD5772	Approved
0.7108	Intermediate Similarity	NPD5773	Approved
0.7103	Intermediate Similarity	NPD6581	Approved
0.7103	Intermediate Similarity	NPD6580	Approved
0.7102	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7281	Phase 3
0.7102	Intermediate Similarity	NPD7280	Phase 3
0.7101	Intermediate Similarity	NPD6037	Discontinued
0.7099	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2986	Phase 2
0.7097	Intermediate Similarity	NPD2989	Phase 2
0.7081	Intermediate Similarity	NPD5297	Approved
0.7073	Intermediate Similarity	NPD4005	Discontinued
0.7065	Intermediate Similarity	NPD8095	Phase 1
0.7062	Intermediate Similarity	NPD6618	Phase 2
0.7059	Intermediate Similarity	NPD1039	Discontinued
0.7059	Intermediate Similarity	NPD3145	Approved
0.7059	Intermediate Similarity	NPD3144	Approved
0.7055	Intermediate Similarity	NPD3445	Approved
0.7055	Intermediate Similarity	NPD1651	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