NPASS Compound

Structure

CID26601 OpenBabel06191715352D 26 30 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 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 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 2 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 4 1 0 0 0 0 3 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 23 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 19 2 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 1 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.17
Volume:	365.198
LogP:	4.357
LogD:	3.435
LogS:	-4.734
# Rotatable Bonds:	2
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	2.956
Fsp3:	0.364
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:	-5.223
MDCK Permeability:	1.9190732928109355e-05
Pgp-inhibitor:	0.371
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.94
Plasma Protein Binding (PPB):	84.18598175048828%
Volume Distribution (VD):	2.076
Pgp-substrate:	8.689973831176758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.791
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	11.214
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.385
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.882
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.951
Carcinogencity:	0.514
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC26601

Natural Product ID:	NPC26601
*Common Name:**	(-)-6-O-Desmethylantofine
IUPAC Name:	(13aR)-2,3-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[10,9-f]indolizin-6-ol
Synonyms:
Standard InCHIKey:	BFZAOGGSKQRCNS-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C22H23NO3/c1-25-21-10-18-16-8-13-4-3-7-23(13)12-20(16)15-6-5-14(24)9-17(15)19(18)11-22(21)26-2/h5-6,9-11,13,24H,3-4,7-8,12H2,1-2H3/p+1/t13-/m1/s1
SMILES:	COc1cc2c3C[C@H]4CCC[NH+]4Cc3c3ccc(cc3c2cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484042
PubChem CID:	9975115
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
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087617]
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24897106]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24981	Dimetia capitellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18056	Silene rubicunda	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18788	Isertia hypoleuca	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18515	Uncaria pilosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14290	Bryonia cretica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17803	Parmelia omphalodes	Species	Parmeliaceae	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
GI50	2
IC50	5
Others	17

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	2
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	86.0	%	PMID[478506]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	86.5	%	PMID[478506]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	87.1	%	PMID[478506]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	89.7	%	PMID[478506]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	92.3	%	PMID[478506]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	94.8	%	PMID[478506]
NPT81	Cell Line	A549	Homo sapiens	GI50	<	1.0	nM	PMID[478506]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	<	1.0	nM	PMID[478506]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1.0	nM	PMID[478511]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	26.0	nM	PMID[478512]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4.0	nM	PMID[478512]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.0	nM	PMID[478505]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10.0	nM	PMID[478505]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	70.0	%	PMID[478507]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	GI	=	70.0	%	PMID[478508]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	70.0	%	PMID[478509]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	42.0	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	72.4	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	33.5	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	65.3	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	35.4	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	60.4	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	40.0	%	PMID[478510]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	70.5	%	PMID[478510]

☑ 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 NPC26601 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	286
0.1-0.2	1443
0.2-0.3	5844
0.3-0.4	11835
0.4-0.5	5586
0.5-0.6	12213
0.6-0.7	4380
0.7-0.8	865
0.8-0.85	191
0.85-0.9	36
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC90844
0.965	High Similarity	NPC95075
0.965	High Similarity	NPC253883
0.9527	High Similarity	NPC186063
0.9517	High Similarity	NPC219162
0.9408	High Similarity	NPC134858
0.9342	High Similarity	NPC233650
0.9315	High Similarity	NPC130941
0.9286	High Similarity	NPC210140
0.9247	High Similarity	NPC144863
0.92	High Similarity	NPC76079
0.9161	High Similarity	NPC150879
0.9122	High Similarity	NPC92541
0.9073	High Similarity	NPC244112
0.898	High Similarity	NPC185838
0.8961	High Similarity	NPC27410
0.8961	High Similarity	NPC166014
0.8917	High Similarity	NPC298979
0.891	High Similarity	NPC169743
0.8903	High Similarity	NPC60186
0.8859	High Similarity	NPC191376
0.8859	High Similarity	NPC321505
0.8859	High Similarity	NPC179825
0.8859	High Similarity	NPC476151
0.88	High Similarity	NPC476571
0.88	High Similarity	NPC135538
0.88	High Similarity	NPC147390
0.88	High Similarity	NPC246587
0.88	High Similarity	NPC24233
0.88	High Similarity	NPC428
0.8759	High Similarity	NPC193528
0.875	High Similarity	NPC326316
0.875	High Similarity	NPC81733
0.8742	High Similarity	NPC103379
0.8742	High Similarity	NPC477565
0.8726	High Similarity	NPC324144
0.8684	High Similarity	NPC192768
0.8684	High Similarity	NPC88249
0.8684	High Similarity	NPC220858
0.8684	High Similarity	NPC97221
0.8684	High Similarity	NPC151895
0.8679	High Similarity	NPC474931
0.8679	High Similarity	NPC12053
0.8679	High Similarity	NPC81218
0.8679	High Similarity	NPC145832
0.8679	High Similarity	NPC306555
0.8679	High Similarity	NPC117188
0.8679	High Similarity	NPC205421
0.8679	High Similarity	NPC158376
0.8671	High Similarity	NPC136508
0.8671	High Similarity	NPC212794
0.8671	High Similarity	NPC196447
0.8671	High Similarity	NPC13504
0.8671	High Similarity	NPC306843
0.8671	High Similarity	NPC96603
0.8671	High Similarity	NPC253043
0.8671	High Similarity	NPC477563
0.8671	High Similarity	NPC78222
0.8639	High Similarity	NPC314682
0.8618	High Similarity	NPC60538
0.8618	High Similarity	NPC207824
0.8616	High Similarity	NPC35627
0.8616	High Similarity	NPC81247
0.8616	High Similarity	NPC476573
0.8608	High Similarity	NPC1229
0.8599	High Similarity	NPC160298
0.8599	High Similarity	NPC266753
0.8599	High Similarity	NPC232924
0.8599	High Similarity	NPC477559
0.8599	High Similarity	NPC306902
0.8581	High Similarity	NPC54379
0.8581	High Similarity	NPC207757
0.8581	High Similarity	NPC295691
0.8581	High Similarity	NPC39701
0.8581	High Similarity	NPC184026
0.8581	High Similarity	NPC193949
0.8581	High Similarity	NPC189266
0.8581	High Similarity	NPC2413
0.8581	High Similarity	NPC278799
0.8581	High Similarity	NPC474915
0.8581	High Similarity	NPC5238
0.8581	High Similarity	NPC328750
0.8581	High Similarity	NPC204828
0.8581	High Similarity	NPC110416
0.8581	High Similarity	NPC276588
0.8581	High Similarity	NPC188163
0.8581	High Similarity	NPC213206
0.8581	High Similarity	NPC469817
0.8581	High Similarity	NPC249797
0.8581	High Similarity	NPC172765
0.8581	High Similarity	NPC127674
0.8537	High Similarity	NPC114364
0.8537	High Similarity	NPC320223
0.8535	High Similarity	NPC111485
0.8535	High Similarity	NPC221864
0.8528	High Similarity	NPC128560
0.8528	High Similarity	NPC199465
0.8528	High Similarity	NPC229166
0.8526	High Similarity	NPC147091
0.8506	High Similarity	NPC277669
0.8506	High Similarity	NPC76213
0.8506	High Similarity	NPC52475
0.8497	Intermediate Similarity	NPC44869
0.8481	Intermediate Similarity	NPC271388
0.8481	Intermediate Similarity	NPC205255
0.8481	Intermediate Similarity	NPC235143
0.8481	Intermediate Similarity	NPC119649
0.8481	Intermediate Similarity	NPC230956
0.8471	Intermediate Similarity	NPC476572
0.8471	Intermediate Similarity	NPC79328
0.8467	Intermediate Similarity	NPC128019
0.8467	Intermediate Similarity	NPC136860
0.8467	Intermediate Similarity	NPC476567
0.8462	Intermediate Similarity	NPC325871
0.8462	Intermediate Similarity	NPC99659
0.8457	Intermediate Similarity	NPC168753
0.8457	Intermediate Similarity	NPC152212
0.8457	Intermediate Similarity	NPC118274
0.8456	Intermediate Similarity	NPC470925
0.8452	Intermediate Similarity	NPC18614
0.8438	Intermediate Similarity	NPC232514
0.8438	Intermediate Similarity	NPC238530
0.8438	Intermediate Similarity	NPC276944
0.8438	Intermediate Similarity	NPC225774
0.8431	Intermediate Similarity	NPC475959
0.8428	Intermediate Similarity	NPC80759
0.8428	Intermediate Similarity	NPC79402
0.8418	Intermediate Similarity	NPC477080
0.8414	Intermediate Similarity	NPC118419
0.8408	Intermediate Similarity	NPC170503
0.8408	Intermediate Similarity	NPC203784
0.8408	Intermediate Similarity	NPC126519
0.8405	Intermediate Similarity	NPC239775
0.8397	Intermediate Similarity	NPC2295
0.8397	Intermediate Similarity	NPC477564
0.8385	Intermediate Similarity	NPC240841
0.8385	Intermediate Similarity	NPC24264
0.8385	Intermediate Similarity	NPC42549
0.8385	Intermediate Similarity	NPC219341
0.8385	Intermediate Similarity	NPC250846
0.8385	Intermediate Similarity	NPC268503
0.8385	Intermediate Similarity	NPC256012
0.8385	Intermediate Similarity	NPC476432
0.8385	Intermediate Similarity	NPC317272
0.8373	Intermediate Similarity	NPC126284
0.8366	Intermediate Similarity	NPC210437
0.8366	Intermediate Similarity	NPC476144
0.8366	Intermediate Similarity	NPC51957
0.8366	Intermediate Similarity	NPC106295
0.8366	Intermediate Similarity	NPC16107
0.8365	Intermediate Similarity	NPC249274
0.8365	Intermediate Similarity	NPC205167
0.8355	Intermediate Similarity	NPC145304
0.8354	Intermediate Similarity	NPC192135
0.8354	Intermediate Similarity	NPC477020
0.8354	Intermediate Similarity	NPC66341
0.8344	Intermediate Similarity	NPC69712
0.8344	Intermediate Similarity	NPC26240
0.8344	Intermediate Similarity	NPC477562
0.8333	Intermediate Similarity	NPC82285
0.8333	Intermediate Similarity	NPC133011
0.8333	Intermediate Similarity	NPC247389
0.8323	Intermediate Similarity	NPC167546
0.8323	Intermediate Similarity	NPC302527
0.8323	Intermediate Similarity	NPC16805
0.8323	Intermediate Similarity	NPC274026
0.8323	Intermediate Similarity	NPC76116
0.8312	Intermediate Similarity	NPC7467
0.8311	Intermediate Similarity	NPC301050
0.8311	Intermediate Similarity	NPC131204
0.8303	Intermediate Similarity	NPC477558
0.8294	Intermediate Similarity	NPC474904
0.8291	Intermediate Similarity	NPC29647
0.8282	Intermediate Similarity	NPC164429
0.8282	Intermediate Similarity	NPC241055
0.8274	Intermediate Similarity	NPC116284
0.8274	Intermediate Similarity	NPC248642
0.8272	Intermediate Similarity	NPC86144
0.8272	Intermediate Similarity	NPC304659
0.8243	Intermediate Similarity	NPC11147
0.8228	Intermediate Similarity	NPC41178
0.8228	Intermediate Similarity	NPC138487
0.8228	Intermediate Similarity	NPC216459
0.8225	Intermediate Similarity	NPC156576
0.8225	Intermediate Similarity	NPC33902
0.8225	Intermediate Similarity	NPC135772
0.8225	Intermediate Similarity	NPC276674
0.8221	Intermediate Similarity	NPC210918
0.8217	Intermediate Similarity	NPC233029
0.8217	Intermediate Similarity	NPC210148
0.8214	Intermediate Similarity	NPC312918
0.8214	Intermediate Similarity	NPC476574
0.8214	Intermediate Similarity	NPC155442
0.8214	Intermediate Similarity	NPC477561
0.821	Intermediate Similarity	NPC168409
0.821	Intermediate Similarity	NPC209377
0.8176	Intermediate Similarity	NPC146288
0.8176	Intermediate Similarity	NPC247639
0.8176	Intermediate Similarity	NPC25084
0.8171	Intermediate Similarity	NPC160570

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 NPC26601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	695
0.2-0.3	884
0.3-0.4	1745
0.4-0.5	2733
0.5-0.6	1914
0.6-0.7	798
0.7-0.8	185
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8581	High Similarity	NPD4664	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD4584	Approved
0.8365	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7831	Phase 2
0.8365	Intermediate Similarity	NPD7833	Phase 2
0.8301	Intermediate Similarity	NPD2421	Approved
0.8301	Intermediate Similarity	NPD2420	Approved
0.8291	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5241	Discontinued
0.8117	Intermediate Similarity	NPD3845	Phase 1
0.8092	Intermediate Similarity	NPD7037	Approved
0.8061	Intermediate Similarity	NPD2898	Approved
0.8038	Intermediate Similarity	NPD4017	Approved
0.7987	Intermediate Similarity	NPD3109	Approved
0.7987	Intermediate Similarity	NPD3110	Approved
0.7952	Intermediate Similarity	NPD2489	Approved
0.7952	Intermediate Similarity	NPD27	Approved
0.7939	Intermediate Similarity	NPD3051	Approved
0.7939	Intermediate Similarity	NPD4010	Discontinued
0.7937	Intermediate Similarity	NPD4773	Phase 2
0.7937	Intermediate Similarity	NPD4772	Phase 2
0.7935	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2970	Approved
0.7892	Intermediate Similarity	NPD2969	Approved
0.7888	Intermediate Similarity	NPD7298	Approved
0.7853	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5718	Phase 2
0.7849	Intermediate Similarity	NPD8054	Approved
0.7849	Intermediate Similarity	NPD8053	Approved
0.78	Intermediate Similarity	NPD4475	Approved
0.78	Intermediate Similarity	NPD4474	Approved
0.7799	Intermediate Similarity	NPD3640	Phase 3
0.7799	Intermediate Similarity	NPD3639	Approved
0.7799	Intermediate Similarity	NPD6030	Approved
0.7799	Intermediate Similarity	NPD6031	Approved
0.7799	Intermediate Similarity	NPD3641	Approved
0.7785	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5155	Approved
0.7785	Intermediate Similarity	NPD5156	Approved
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6788	Approved
0.7725	Intermediate Similarity	NPD6071	Discontinued
0.7718	Intermediate Similarity	NPD3595	Approved
0.7718	Intermediate Similarity	NPD2606	Approved
0.7718	Intermediate Similarity	NPD3594	Approved
0.7718	Intermediate Similarity	NPD2605	Approved
0.7692	Intermediate Similarity	NPD4236	Phase 3
0.7692	Intermediate Similarity	NPD5177	Phase 3
0.7692	Intermediate Similarity	NPD4237	Approved
0.7683	Intermediate Similarity	NPD5978	Approved
0.7683	Intermediate Similarity	NPD5977	Approved
0.7683	Intermediate Similarity	NPD2560	Approved
0.7683	Intermediate Similarity	NPD2563	Approved
0.7665	Intermediate Similarity	NPD7802	Discontinued
0.7651	Intermediate Similarity	NPD3635	Approved
0.7651	Intermediate Similarity	NPD3637	Approved
0.7651	Intermediate Similarity	NPD3636	Approved
0.7651	Intermediate Similarity	NPD7400	Phase 3
0.7647	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8252	Approved
0.7647	Intermediate Similarity	NPD8251	Approved
0.7647	Intermediate Similarity	NPD8099	Discontinued
0.7639	Intermediate Similarity	NPD4093	Discontinued
0.763	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6090	Discontinued
0.7619	Intermediate Similarity	NPD1669	Approved
0.7614	Intermediate Similarity	NPD7906	Approved
0.761	Intermediate Similarity	NPD7598	Phase 2
0.7602	Intermediate Similarity	NPD8156	Discontinued
0.76	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4577	Approved
0.7586	Intermediate Similarity	NPD4578	Approved
0.7566	Intermediate Similarity	NPD2674	Phase 3
0.7562	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6331	Phase 2
0.7529	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4166	Phase 2
0.7514	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3124	Discontinued
0.7486	Intermediate Similarity	NPD7311	Approved
0.7486	Intermediate Similarity	NPD7313	Approved
0.7486	Intermediate Similarity	NPD7312	Approved
0.7486	Intermediate Similarity	NPD7310	Approved
0.7485	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5604	Discontinued
0.7484	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6896	Approved
0.7484	Intermediate Similarity	NPD6895	Approved
0.7468	Intermediate Similarity	NPD3060	Approved
0.7467	Intermediate Similarity	NPD6584	Phase 3
0.7466	Intermediate Similarity	NPD2668	Approved
0.7466	Intermediate Similarity	NPD2667	Approved
0.7458	Intermediate Similarity	NPD4663	Approved
0.7457	Intermediate Similarity	NPD7479	Phase 2
0.7455	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7309	Approved
0.7432	Intermediate Similarity	NPD2233	Approved
0.7432	Intermediate Similarity	NPD2232	Approved
0.7432	Intermediate Similarity	NPD2230	Approved
0.743	Intermediate Similarity	NPD2488	Approved
0.743	Intermediate Similarity	NPD2490	Approved
0.7427	Intermediate Similarity	NPD4481	Phase 3
0.7421	Intermediate Similarity	NPD6748	Discontinued
0.7414	Intermediate Similarity	NPD6297	Approved
0.7407	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7438	Suspended
0.7386	Intermediate Similarity	NPD7294	Phase 1
0.7386	Intermediate Similarity	NPD3145	Approved
0.7386	Intermediate Similarity	NPD3144	Approved
0.7386	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1914	Approved
0.7362	Intermediate Similarity	NPD5976	Discontinued
0.7362	Intermediate Similarity	NPD7427	Discontinued
0.7337	Intermediate Similarity	NPD5709	Phase 3
0.7325	Intermediate Similarity	NPD1753	Discontinued
0.731	Intermediate Similarity	NPD6747	Phase 1
0.7305	Intermediate Similarity	NPD5773	Approved
0.7305	Intermediate Similarity	NPD5772	Approved
0.7305	Intermediate Similarity	NPD2977	Approved
0.7305	Intermediate Similarity	NPD2978	Approved
0.7299	Intermediate Similarity	NPD4873	Discontinued
0.7296	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4666	Phase 3
0.729	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3620	Phase 2
0.7278	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6582	Phase 2
0.7267	Intermediate Similarity	NPD6583	Phase 3
0.7256	Intermediate Similarity	NPD2122	Discontinued
0.7256	Intermediate Similarity	NPD4727	Phase 1
0.7251	Intermediate Similarity	NPD6107	Approved
0.7247	Intermediate Similarity	NPD6853	Approved
0.7247	Intermediate Similarity	NPD6851	Approved
0.7239	Intermediate Similarity	NPD7019	Approved
0.7239	Intermediate Similarity	NPD4123	Phase 3
0.7239	Intermediate Similarity	NPD7020	Approved
0.7238	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4721	Approved
0.7233	Intermediate Similarity	NPD7030	Discontinued
0.7233	Intermediate Similarity	NPD4725	Approved
0.7233	Intermediate Similarity	NPD4726	Approved
0.7222	Intermediate Similarity	NPD7291	Discontinued
0.7205	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5754	Discontinued
0.7197	Intermediate Similarity	NPD2492	Phase 1
0.7191	Intermediate Similarity	NPD2971	Approved
0.7191	Intermediate Similarity	NPD7281	Phase 3
0.7191	Intermediate Similarity	NPD7280	Phase 3
0.7191	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2968	Approved
0.7186	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7110	Phase 1
0.7184	Intermediate Similarity	NPD5938	Phase 3
0.7176	Intermediate Similarity	NPD4055	Discovery
0.7171	Intermediate Similarity	NPD3055	Approved
0.7171	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4103	Phase 2
0.7171	Intermediate Similarity	NPD3053	Approved
0.7169	Intermediate Similarity	NPD4005	Discontinued
0.7168	Intermediate Similarity	NPD6688	Approved
0.7168	Intermediate Similarity	NPD6687	Approved
0.716	Intermediate Similarity	NPD5160	Discontinued
0.716	Intermediate Similarity	NPD3301	Approved
0.7152	Intermediate Similarity	NPD4659	Approved
0.7143	Intermediate Similarity	NPD4162	Approved
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7124	Intermediate Similarity	NPD7018	Phase 2
0.7117	Intermediate Similarity	NPD7124	Phase 2
0.7115	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7477	Discontinued
0.7114	Intermediate Similarity	NPD1751	Approved
0.7107	Intermediate Similarity	NPD4108	Discontinued
0.7103	Intermediate Similarity	NPD5283	Phase 1
0.7099	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5304	Approved
0.7095	Intermediate Similarity	NPD5303	Approved
0.7095	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4097	Suspended
0.7081	Intermediate Similarity	NPD5582	Discontinued
0.7074	Intermediate Similarity	NPD3452	Approved
0.7074	Intermediate Similarity	NPD3450	Approved
0.7074	Intermediate Similarity	NPD2493	Approved
0.7074	Intermediate Similarity	NPD2494	Approved
0.7073	Intermediate Similarity	NPD7213	Phase 3
0.7073	Intermediate Similarity	NPD7212	Phase 2
0.707	Intermediate Similarity	NPD2238	Phase 2
0.7063	Intermediate Similarity	NPD2161	Phase 2
0.7056	Intermediate Similarity	NPD6556	Clinical (unspecified phase)

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