NPASS Compound

Structure

NPC476220 OpenBabel07101718302D 43 49 0 0 1 0 0 0 0 0999 V2000 1.1148 -3.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3005 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1828 -2.1155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6875 -5.0199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0351 -0.7285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3577 -0.0541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0240 -2.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2058 -3.6112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6990 -3.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6875 -3.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6875 -2.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6217 -2.8256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2669 -1.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0319 -3.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1128 -1.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6291 -1.4129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5548 -1.5796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4988 -2.2251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1917 -1.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0216 -2.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8597 -3.5861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0742 -1.4459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0319 -2.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8597 -1.6745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8671 -1.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1897 -1.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2558 -1.2652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8278 -0.4779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0989 -2.6501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4239 -2.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 -1.5508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3216 -1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7103 -0.6396 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6609 -0.7395 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5133 -1.1844 0.0000 N 0 3 3 0 0 0 0 0 0 0 0 0 -1.8536 -3.5739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2534 -3.1490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8597 -4.5420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7898 -1.6523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4350 -0.3035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3467 -2.7240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4215 -1.9757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 7 41 1 0 0 0 0 8 19 2 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 20 2 0 0 0 0 13 26 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 35 1 0 0 0 0 18 31 1 0 0 0 0 18 42 1 0 0 0 0 19 22 1 0 0 0 0 20 29 1 0 0 0 0 21 38 1 0 0 0 0 22 31 1 6 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 34 1 0 0 0 0 25 26 2 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 33 1 6 0 0 0 27 35 1 0 0 0 0 28 35 1 1 0 0 0 28 43 1 0 0 0 0 29 36 2 0 0 0 0 29 42 1 0 0 0 0 30 31 1 0 0 0 0 30 37 2 0 0 0 0 30 41 1 0 0 0 0 31 32 1 1 0 0 0 32 33 1 1 0 0 0 33 34 1 0 0 0 0 33 43 1 6 0 0 0 M CHG 1 35 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	591.27
Volume:	589.334
LogP:	2.976
LogD:	3.541
LogS:	-3.166
# Rotatable Bonds:	9
TPSA:	92.76
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	6.594
Fsp3:	0.515
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.517
MDCK Permeability:	3.991816265624948e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	72.14726257324219%
Volume Distribution (VD):	1.836
Pgp-substrate:	22.824974060058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.383
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.48
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	10.4
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.346
AMES Toxicity:	0.497
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.178
Carcinogencity:	0.981
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476220

Natural Product ID:	NPC476220
*Common Name:**	Alstiphyllanine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FEWCKFKZLJXUMP-GMHDAERMSA-N
Standard InCHI:	InChI=1S/C33H39N2O8/c1-8-19-17-35(3)27-15-22(19)31(30(37)41-7,18-42-29(36)20-9-12-25(39-5)26(13-20)40-6)32-16-28(35)43-33(27,32)34(2)24-11-10-21(38-4)14-23(24)32/h8-14,22,27-28H,15-18H2,1-7H3/q+1/b19-8-/t22-,27-,28-,31-,32-,33-,35?/m0/s1
SMILES:	CC=C1C[N+]2(C3CC1C(C45C3(N(C6=C4C=C(C=C6)OC)C)OC2C5)(COC(=O)C7=CC(=C(C=C7)OC)OC)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555254
PubChem CID:	45270514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type alkaloids

*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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[454230]
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	-10.3	%	PMID[454231]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	-0.2	%	PMID[454231]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.34	ug.mL-1	PMID[454230]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	35.0	%	PMID[454230]

☑ 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 NPC476220 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	425
0.1-0.2	1827
0.2-0.3	4815
0.3-0.4	11614
0.4-0.5	8903
0.5-0.6	13102
0.6-0.7	1801
0.7-0.8	199
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160113
0.981	High Similarity	NPC476258
0.981	High Similarity	NPC304837
0.9583	High Similarity	NPC120239
0.9575	High Similarity	NPC154922
0.9444	High Similarity	NPC113455
0.8863	High Similarity	NPC234772
0.8796	High Similarity	NPC231924
0.8416	Intermediate Similarity	NPC476436
0.8311	Intermediate Similarity	NPC476429
0.8133	Intermediate Similarity	NPC473458
0.7974	Intermediate Similarity	NPC471513
0.7973	Intermediate Similarity	NPC195636
0.7957	Intermediate Similarity	NPC477393
0.789	Intermediate Similarity	NPC477396
0.7872	Intermediate Similarity	NPC477395
0.7867	Intermediate Similarity	NPC476069
0.7854	Intermediate Similarity	NPC131977
0.7847	Intermediate Similarity	NPC21425
0.7835	Intermediate Similarity	NPC139373
0.7834	Intermediate Similarity	NPC207971
0.7822	Intermediate Similarity	NPC288110
0.7788	Intermediate Similarity	NPC318525
0.7788	Intermediate Similarity	NPC10653
0.7778	Intermediate Similarity	NPC120671
0.7778	Intermediate Similarity	NPC226652
0.7778	Intermediate Similarity	NPC314100
0.7778	Intermediate Similarity	NPC72788
0.7753	Intermediate Similarity	NPC128476
0.7749	Intermediate Similarity	NPC223242
0.7745	Intermediate Similarity	NPC301501
0.7729	Intermediate Similarity	NPC19175
0.7717	Intermediate Similarity	NPC268077
0.7714	Intermediate Similarity	NPC191489
0.7713	Intermediate Similarity	NPC159815
0.7685	Intermediate Similarity	NPC215098
0.7685	Intermediate Similarity	NPC70290
0.7685	Intermediate Similarity	NPC73020
0.7685	Intermediate Similarity	NPC46744
0.7685	Intermediate Similarity	NPC124302
0.7685	Intermediate Similarity	NPC14622
0.7672	Intermediate Similarity	NPC477397
0.7657	Intermediate Similarity	NPC329932
0.7647	Intermediate Similarity	NPC469451
0.7647	Intermediate Similarity	NPC469452
0.7639	Intermediate Similarity	NPC90967
0.7637	Intermediate Similarity	NPC469450
0.7634	Intermediate Similarity	NPC127996
0.7634	Intermediate Similarity	NPC10732
0.7628	Intermediate Similarity	NPC34717
0.7604	Intermediate Similarity	NPC71124
0.7602	Intermediate Similarity	NPC476500
0.7594	Intermediate Similarity	NPC181928
0.759	Intermediate Similarity	NPC315634
0.759	Intermediate Similarity	NPC100734
0.759	Intermediate Similarity	NPC88923
0.7585	Intermediate Similarity	NPC291173
0.7569	Intermediate Similarity	NPC5374
0.7557	Intermediate Similarity	NPC475147
0.7545	Intermediate Similarity	NPC2173
0.7545	Intermediate Similarity	NPC202771
0.7545	Intermediate Similarity	NPC119818
0.7545	Intermediate Similarity	NPC328700
0.7544	Intermediate Similarity	NPC87560
0.7544	Intermediate Similarity	NPC195120
0.7523	Intermediate Similarity	NPC195787
0.7523	Intermediate Similarity	NPC246140
0.7522	Intermediate Similarity	NPC268223
0.7511	Intermediate Similarity	NPC222046
0.75	Intermediate Similarity	NPC475133
0.7489	Intermediate Similarity	NPC308943
0.7489	Intermediate Similarity	NPC55470
0.7478	Intermediate Similarity	NPC118154
0.7478	Intermediate Similarity	NPC157983
0.7467	Intermediate Similarity	NPC77777
0.7455	Intermediate Similarity	NPC138830
0.7442	Intermediate Similarity	NPC141440
0.7427	Intermediate Similarity	NPC469722
0.7419	Intermediate Similarity	NPC254957
0.7393	Intermediate Similarity	NPC35680
0.739	Intermediate Similarity	NPC284685
0.7389	Intermediate Similarity	NPC269449
0.7375	Intermediate Similarity	NPC151171
0.7362	Intermediate Similarity	NPC248903
0.7361	Intermediate Similarity	NPC473298
0.7339	Intermediate Similarity	NPC148124
0.7339	Intermediate Similarity	NPC94499
0.7325	Intermediate Similarity	NPC119722
0.7319	Intermediate Similarity	NPC26928
0.7297	Intermediate Similarity	NPC474427
0.7296	Intermediate Similarity	NPC99724
0.7296	Intermediate Similarity	NPC118189
0.7284	Intermediate Similarity	NPC256422
0.7281	Intermediate Similarity	NPC82541
0.7277	Intermediate Similarity	NPC115588
0.7277	Intermediate Similarity	NPC477394
0.7269	Intermediate Similarity	NPC473781
0.7269	Intermediate Similarity	NPC470631
0.7269	Intermediate Similarity	NPC35390
0.7257	Intermediate Similarity	NPC478075
0.7257	Intermediate Similarity	NPC222561
0.7241	Intermediate Similarity	NPC182853
0.724	Intermediate Similarity	NPC474432
0.724	Intermediate Similarity	NPC475713
0.7238	Intermediate Similarity	NPC473486
0.7238	Intermediate Similarity	NPC475316
0.7232	Intermediate Similarity	NPC286135
0.7225	Intermediate Similarity	NPC100573
0.7225	Intermediate Similarity	NPC207873
0.7222	Intermediate Similarity	NPC76478
0.722	Intermediate Similarity	NPC67904
0.7215	Intermediate Similarity	NPC226708
0.7207	Intermediate Similarity	NPC193906
0.7207	Intermediate Similarity	NPC23080
0.7205	Intermediate Similarity	NPC295479
0.7205	Intermediate Similarity	NPC220241
0.7198	Intermediate Similarity	NPC126556
0.7195	Intermediate Similarity	NPC33256
0.7168	Intermediate Similarity	NPC87714
0.7167	Intermediate Similarity	NPC134702
0.7162	Intermediate Similarity	NPC66909
0.7156	Intermediate Similarity	NPC162694
0.7156	Intermediate Similarity	NPC1464
0.7149	Intermediate Similarity	NPC46259
0.7143	Intermediate Similarity	NPC227361
0.7143	Intermediate Similarity	NPC13249
0.7143	Intermediate Similarity	NPC124658
0.7143	Intermediate Similarity	NPC127178
0.7143	Intermediate Similarity	NPC470480
0.7137	Intermediate Similarity	NPC80472
0.7136	Intermediate Similarity	NPC329992
0.7112	Intermediate Similarity	NPC148391
0.7111	Intermediate Similarity	NPC311781
0.7111	Intermediate Similarity	NPC471512
0.7111	Intermediate Similarity	NPC471489
0.711	Intermediate Similarity	NPC214629
0.7104	Intermediate Similarity	NPC302001
0.7101	Intermediate Similarity	NPC285254
0.71	Intermediate Similarity	NPC470482
0.71	Intermediate Similarity	NPC470481
0.7091	Intermediate Similarity	NPC25401
0.7083	Intermediate Similarity	NPC27887
0.7076	Intermediate Similarity	NPC7560
0.7074	Intermediate Similarity	NPC90185
0.7059	Intermediate Similarity	NPC122886
0.7056	Intermediate Similarity	NPC186569
0.7056	Intermediate Similarity	NPC61731
0.7054	Intermediate Similarity	NPC83019
0.7054	Intermediate Similarity	NPC100863
0.7051	Intermediate Similarity	NPC115906
0.7046	Intermediate Similarity	NPC251071
0.7045	Intermediate Similarity	NPC312531
0.7043	Intermediate Similarity	NPC46990
0.704	Intermediate Similarity	NPC470646
0.7039	Intermediate Similarity	NPC189661
0.7039	Intermediate Similarity	NPC298449
0.7037	Intermediate Similarity	NPC190461
0.7035	Intermediate Similarity	NPC201055
0.7035	Intermediate Similarity	NPC151470
0.7035	Intermediate Similarity	NPC64576
0.7035	Intermediate Similarity	NPC254045
0.7034	Intermediate Similarity	NPC140311
0.7018	Intermediate Similarity	NPC38961
0.7014	Intermediate Similarity	NPC22476
0.7009	Intermediate Similarity	NPC204580
0.7005	Intermediate Similarity	NPC220961
0.7004	Intermediate Similarity	NPC475747
0.6996	Remote Similarity	NPC195788
0.6996	Remote Similarity	NPC473006
0.6996	Remote Similarity	NPC114468
0.6996	Remote Similarity	NPC237901
0.6992	Remote Similarity	NPC223590
0.6985	Remote Similarity	NPC471303
0.6982	Remote Similarity	NPC63152
0.6979	Remote Similarity	NPC473837
0.6978	Remote Similarity	NPC17677
0.6975	Remote Similarity	NPC106593
0.6972	Remote Similarity	NPC473562
0.697	Remote Similarity	NPC476496
0.6968	Remote Similarity	NPC208890
0.6968	Remote Similarity	NPC237579
0.6966	Remote Similarity	NPC2905
0.6964	Remote Similarity	NPC125924
0.6964	Remote Similarity	NPC174783
0.6964	Remote Similarity	NPC477258
0.6957	Remote Similarity	NPC326895
0.6953	Remote Similarity	NPC116178
0.6943	Remote Similarity	NPC470484
0.693	Remote Similarity	NPC473005
0.693	Remote Similarity	NPC227683
0.6926	Remote Similarity	NPC106840
0.6926	Remote Similarity	NPC94687
0.6926	Remote Similarity	NPC476495
0.6923	Remote Similarity	NPC230098
0.6923	Remote Similarity	NPC477259
0.6923	Remote Similarity	NPC217903
0.6923	Remote Similarity	NPC169387
0.6923	Remote Similarity	NPC30749
0.6923	Remote Similarity	NPC321166
0.692	Remote Similarity	NPC469816

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 NPC476220 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	641
0.2-0.3	942
0.3-0.4	2033
0.4-0.5	2936
0.5-0.6	1907
0.6-0.7	409
0.7-0.8	28
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
0.7802	Intermediate Similarity	NPD6625	Approved
0.7714	Intermediate Similarity	NPD7708	Approved
0.7685	Intermediate Similarity	NPD4420	Approved
0.759	Intermediate Similarity	NPD7803	Approved
0.7553	Intermediate Similarity	NPD4846	Phase 2
0.7545	Intermediate Similarity	NPD5006	Approved
0.7545	Intermediate Similarity	NPD5005	Approved
0.7414	Intermediate Similarity	NPD6997	Phase 2
0.739	Intermediate Similarity	NPD7955	Approved
0.739	Intermediate Similarity	NPD7956	Approved
0.7382	Intermediate Similarity	NPD7278	Phase 2
0.7382	Intermediate Similarity	NPD7279	Phase 2
0.7364	Intermediate Similarity	NPD5071	Phase 2
0.7261	Intermediate Similarity	NPD7048	Phase 3
0.7253	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7907	Approved
0.722	Intermediate Similarity	NPD4107	Approved
0.721	Intermediate Similarity	NPD2899	Discontinued
0.7162	Intermediate Similarity	NPD2973	Approved
0.7162	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2974	Approved
0.7162	Intermediate Similarity	NPD2975	Approved
0.7155	Intermediate Similarity	NPD7047	Phase 3
0.7143	Intermediate Similarity	NPD4580	Approved
0.7137	Intermediate Similarity	NPD7922	Phase 1
0.7117	Intermediate Similarity	NPD5582	Discontinued
0.7111	Intermediate Similarity	NPD4482	Phase 3
0.7098	Intermediate Similarity	NPD6874	Approved
0.7082	Intermediate Similarity	NPD8149	Discontinued
0.707	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6723	Discontinued
0.7051	Intermediate Similarity	NPD2968	Approved
0.7051	Intermediate Similarity	NPD2971	Approved
0.7048	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3450	Approved
0.7035	Intermediate Similarity	NPD2494	Approved
0.7035	Intermediate Similarity	NPD3452	Approved
0.7035	Intermediate Similarity	NPD2493	Approved
0.7028	Intermediate Similarity	NPD5242	Approved
0.7018	Intermediate Similarity	NPD4582	Approved
0.7018	Intermediate Similarity	NPD4583	Approved
0.7013	Intermediate Similarity	NPD5860	Discontinued
0.7004	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4859	Phase 1
0.6996	Remote Similarity	NPD8467	Approved
0.6996	Remote Similarity	NPD8465	Approved
0.6996	Remote Similarity	NPD8466	Approved
0.6992	Remote Similarity	NPD4665	Approved
0.6992	Remote Similarity	NPD4111	Phase 1
0.6991	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4004	Approved
0.6974	Remote Similarity	NPD4002	Approved
0.6974	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3437	Discontinued
0.6958	Remote Similarity	NPD7186	Phase 3
0.6957	Remote Similarity	NPD6386	Approved
0.6957	Remote Similarity	NPD6385	Approved
0.6946	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7805	Phase 3
0.691	Remote Similarity	NPD5676	Approved
0.69	Remote Similarity	NPD7497	Discontinued
0.6894	Remote Similarity	NPD7559	Phase 2
0.6891	Remote Similarity	NPD8425	Approved
0.6891	Remote Similarity	NPD8426	Approved
0.6891	Remote Similarity	NPD8459	Approved
0.6891	Remote Similarity	NPD8460	Approved
0.6886	Remote Similarity	NPD6321	Discontinued
0.688	Remote Similarity	NPD7225	Discontinued
0.6875	Remote Similarity	NPD3912	Discontinued
0.6868	Remote Similarity	NPD8429	Approved
0.6868	Remote Similarity	NPD8427	Approved
0.6868	Remote Similarity	NPD8428	Approved
0.6867	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3057	Approved
0.6853	Remote Similarity	NPD4082	Approved
0.6852	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4481	Phase 3
0.6835	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8463	Approved
0.6822	Remote Similarity	NPD5186	Approved
0.6822	Remote Similarity	NPD5183	Approved
0.682	Remote Similarity	NPD5600	Discontinued
0.682	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7223	Discontinued
0.6818	Remote Similarity	NPD7224	Discontinued
0.6816	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6238	Discontinued
0.6809	Remote Similarity	NPD8461	Discontinued
0.6805	Remote Similarity	NPD7820	Phase 3
0.68	Remote Similarity	NPD6716	Phase 1
0.6787	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7560	Approved
0.6786	Remote Similarity	NPD2490	Approved
0.6786	Remote Similarity	NPD2488	Approved
0.6783	Remote Similarity	NPD7626	Approved
0.6783	Remote Similarity	NPD2972	Approved
0.6783	Remote Similarity	NPD7627	Approved
0.6783	Remote Similarity	NPD3533	Approved
0.6781	Remote Similarity	NPD2906	Approved
0.6781	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2907	Approved
0.6771	Remote Similarity	NPD7906	Approved
0.6771	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8363	Approved
0.6768	Remote Similarity	NPD8364	Approved
0.6767	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD683	Approved
0.6765	Remote Similarity	NPD5980	Discovery
0.6759	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5313	Approved
0.6743	Remote Similarity	NPD5312	Approved
0.6741	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7827	Phase 1
0.6737	Remote Similarity	NPD4492	Approved
0.6737	Remote Similarity	NPD4494	Approved
0.6727	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4040	Phase 1
0.672	Remote Similarity	NPD7885	Phase 2
0.672	Remote Similarity	NPD7886	Phase 2
0.6719	Remote Similarity	NPD5488	Discontinued
0.6717	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6853	Approved
0.6712	Remote Similarity	NPD6851	Approved
0.671	Remote Similarity	NPD2491	Approved
0.671	Remote Similarity	NPD3448	Approved
0.6698	Remote Similarity	NPD2680	Approved
0.6698	Remote Similarity	NPD2247	Approved
0.6698	Remote Similarity	NPD6457	Approved
0.6698	Remote Similarity	NPD5977	Approved
0.6698	Remote Similarity	NPD2249	Approved
0.6698	Remote Similarity	NPD2681	Approved
0.6698	Remote Similarity	NPD5978	Approved
0.6695	Remote Similarity	NPD4493	Discontinued
0.6667	Remote Similarity	NPD7281	Phase 3
0.6667	Remote Similarity	NPD8492	Approved
0.6667	Remote Similarity	NPD7280	Phase 3
0.6667	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6199	Discontinued
0.6653	Remote Similarity	NPD5025	Approved
0.6652	Remote Similarity	NPD7811	Phase 3
0.6652	Remote Similarity	NPD7810	Phase 3
0.6639	Remote Similarity	NPD5496	Approved
0.6639	Remote Similarity	NPD4455	Discontinued
0.6624	Remote Similarity	NPD1945	Phase 1
0.6624	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5353	Approved
0.6619	Remote Similarity	NPD8489	Phase 1
0.6615	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3888	Discontinued
0.6596	Remote Similarity	NPD4596	Phase 1
0.6594	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5928	Phase 1
0.6586	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3297	Approved
0.658	Remote Similarity	NPD8285	Discontinued
0.6579	Remote Similarity	NPD7262	Phase 1
0.6576	Remote Similarity	NPD8367	Approved
0.6568	Remote Similarity	NPD4022	Approved
0.6568	Remote Similarity	NPD3472	Approved
0.6562	Remote Similarity	NPD6618	Phase 2
0.6562	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7417	Discontinued
0.6561	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6873	Phase 2
0.6556	Remote Similarity	NPD8404	Phase 2
0.6549	Remote Similarity	NPD7291	Discontinued
0.6549	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4885	Approved
0.6545	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6107	Approved
0.6541	Remote Similarity	NPD7924	Phase 2
0.6541	Remote Similarity	NPD7925	Phase 2
0.6535	Remote Similarity	NPD7296	Approved
0.6534	Remote Similarity	NPD3006	Discontinued
0.6532	Remote Similarity	NPD6297	Approved
0.6525	Remote Similarity	NPD6296	Discontinued
0.6518	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4577	Approved
0.6518	Remote Similarity	NPD4578	Approved
0.6516	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3051	Approved
0.6513	Remote Similarity	NPD3893	Discontinued
0.6513	Remote Similarity	NPD3372	Discontinued
0.6511	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD3298	Approved
0.6511	Remote Similarity	NPD7891	Discontinued
0.6509	Remote Similarity	NPD5609	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