NPASS Compound

Structure

NPC201607 OpenBabel07101719132D 43 47 0 0 1 0 0 0 0 0999 V2000 2.5996 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8186 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3291 -0.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4152 0.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5428 -0.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2955 -2.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2955 1.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4213 0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9231 -0.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2702 1.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9915 -0.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9915 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0829 1.5822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2440 1.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 0.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8629 1.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4475 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3834 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7516 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8719 0.5545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5996 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9915 -1.0799 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2955 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8395 -2.5486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6162 0.7610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2314 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5354 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5996 -0.1007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8395 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5940 0.7097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 -1.5695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2955 -0.1007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4475 0.3889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9141 0.3509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9036 -3.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0794 -3.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2314 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5354 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1273 1.5309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7516 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6875 -3.0382 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 20 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 7 33 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 26 1 0 0 0 0 14 32 1 0 0 0 0 15 34 1 0 0 0 0 16 33 1 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 36 2 0 0 0 0 20 41 1 0 0 0 0 21 10 1 1 0 0 0 21 29 1 0 0 0 0 21 35 1 0 0 0 0 22 29 1 0 0 0 0 22 41 1 1 0 0 0 23 30 1 0 0 0 0 23 32 1 1 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 42 1 6 0 0 0 26 31 1 1 0 0 0 26 43 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 28 39 2 0 0 0 0 28 42 1 0 0 0 0 29 34 1 6 0 0 0 31 40 1 0 0 0 0 32 6 1 1 0 0 0 33 34 1 6 0 0 0 34 8 1 6 0 0 0 35 9 1 6 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.4
Volume:	633.546
LogP:	4.865
LogD:	4.344
LogS:	-4.396
# Rotatable Bonds:	8
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	5.166
Fsp3:	0.914
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.273
MDCK Permeability:	4.220860864734277e-05
Pgp-inhibitor:	0.92
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.508

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	88.27735137939453%
Volume Distribution (VD):	0.606
Pgp-substrate:	4.035004615783691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.671
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	2.404
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.901
Carcinogencity:	0.014
Eye Corrosion:	0.634
Eye Irritation:	0.47
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: NPC201607

Natural Product ID:	NPC201607
*Common Name:**	Papyriferic Acid
IUPAC Name:	3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-oxopropanoic acid
Synonyms:	Papyriferic Acid
Standard InCHIKey:	RLVAVWQAAQFUOP-GNYBQDBLSA-N
Standard InCHI:	InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)/t21-,22+,23-,24+,25+,26+,29-,32-,33+,34+,35-/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](C(C)(C)[C@@H]3CC[C@@]2(C)[C@]2(C)CC[C@@H]([C@@H]12)[C@]1(C)CC[C@H](C(C)(C)O)O1)OC(=O)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224050
PubChem CID:	441683
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	47800.0	nM	PMID[530626]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	47600.0	nM	PMID[530626]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	71700.0	nM	PMID[530626]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	52200.0	nM	PMID[530626]
NPT27	Others	Unspecified		IC50	=	66000.0	nM	PMID[530626]
NPT27	Others	Unspecified		IC50	=	60100.0	nM	PMID[530626]
NPT27	Others	Unspecified		IC50	=	42500.0	nM	PMID[530626]
NPT27	Others	Unspecified		IC50	=	34500.0	nM	PMID[530626]

☑ 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 NPC201607 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	399
0.1-0.2	3408
0.2-0.3	10072
0.3-0.4	13544
0.4-0.5	5676
0.5-0.6	5094
0.6-0.7	3559
0.7-0.8	869
0.8-0.85	54
0.85-0.9	10
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC56777
0.9756	High Similarity	NPC114378
0.9756	High Similarity	NPC103782
0.9286	High Similarity	NPC477283
0.9268	High Similarity	NPC286719
0.9268	High Similarity	NPC477286
0.9157	High Similarity	NPC477285
0.9157	High Similarity	NPC111582
0.9146	High Similarity	NPC190940
0.9059	High Similarity	NPC215968
0.9059	High Similarity	NPC155531
0.881	High Similarity	NPC477284
0.8764	High Similarity	NPC473066
0.8675	High Similarity	NPC477287
0.8588	High Similarity	NPC154043
0.8588	High Similarity	NPC202688
0.8588	High Similarity	NPC60018
0.8587	High Similarity	NPC116683
0.8452	Intermediate Similarity	NPC81074
0.8452	Intermediate Similarity	NPC477282
0.8434	Intermediate Similarity	NPC133596
0.8434	Intermediate Similarity	NPC212453
0.8434	Intermediate Similarity	NPC64081
0.8434	Intermediate Similarity	NPC11907
0.8434	Intermediate Similarity	NPC474574
0.8387	Intermediate Similarity	NPC237071
0.8387	Intermediate Similarity	NPC238796
0.8387	Intermediate Similarity	NPC203434
0.8295	Intermediate Similarity	NPC266651
0.8261	Intermediate Similarity	NPC182740
0.8261	Intermediate Similarity	NPC256104
0.8261	Intermediate Similarity	NPC122083
0.8261	Intermediate Similarity	NPC211845
0.8256	Intermediate Similarity	NPC470154
0.8256	Intermediate Similarity	NPC73515
0.8235	Intermediate Similarity	NPC476176
0.8235	Intermediate Similarity	NPC220379
0.8193	Intermediate Similarity	NPC270306
0.8193	Intermediate Similarity	NPC231680
0.8193	Intermediate Similarity	NPC91387
0.8191	Intermediate Similarity	NPC156377
0.8172	Intermediate Similarity	NPC151214
0.8172	Intermediate Similarity	NPC191915
0.8161	Intermediate Similarity	NPC477446
0.8161	Intermediate Similarity	NPC311642
0.8161	Intermediate Similarity	NPC164289
0.8161	Intermediate Similarity	NPC477447
0.8161	Intermediate Similarity	NPC475388
0.8161	Intermediate Similarity	NPC100366
0.8161	Intermediate Similarity	NPC13494
0.8161	Intermediate Similarity	NPC470155
0.8161	Intermediate Similarity	NPC242771
0.814	Intermediate Similarity	NPC472951
0.814	Intermediate Similarity	NPC472943
0.8132	Intermediate Similarity	NPC82955
0.8118	Intermediate Similarity	NPC471045
0.8085	Intermediate Similarity	NPC94582
0.8085	Intermediate Similarity	NPC57964
0.8072	Intermediate Similarity	NPC472944
0.8072	Intermediate Similarity	NPC472945
0.8068	Intermediate Similarity	NPC470070
0.8068	Intermediate Similarity	NPC268578
0.8068	Intermediate Similarity	NPC217559
0.8068	Intermediate Similarity	NPC292458
0.8046	Intermediate Similarity	NPC470156
0.8043	Intermediate Similarity	NPC470114
0.8041	Intermediate Similarity	NPC475574
0.8041	Intermediate Similarity	NPC108227
0.8041	Intermediate Similarity	NPC472081
0.8041	Intermediate Similarity	NPC476512
0.8022	Intermediate Similarity	NPC471221
0.8021	Intermediate Similarity	NPC292775
0.8	Intermediate Similarity	NPC252056
0.8	Intermediate Similarity	NPC131365
0.8	Intermediate Similarity	NPC80700
0.8	Intermediate Similarity	NPC171658
0.7978	Intermediate Similarity	NPC473336
0.7978	Intermediate Similarity	NPC319909
0.7978	Intermediate Similarity	NPC471044
0.7978	Intermediate Similarity	NPC18953
0.7959	Intermediate Similarity	NPC470029
0.7959	Intermediate Similarity	NPC114700
0.7959	Intermediate Similarity	NPC134967
0.7959	Intermediate Similarity	NPC310138
0.7957	Intermediate Similarity	NPC229801
0.7957	Intermediate Similarity	NPC210759
0.7957	Intermediate Similarity	NPC307167
0.7955	Intermediate Similarity	NPC148740
0.7955	Intermediate Similarity	NPC121121
0.7955	Intermediate Similarity	NPC102156
0.7955	Intermediate Similarity	NPC477936
0.7938	Intermediate Similarity	NPC470030
0.7935	Intermediate Similarity	NPC20822
0.7935	Intermediate Similarity	NPC24705
0.7935	Intermediate Similarity	NPC56962
0.7931	Intermediate Similarity	NPC474714
0.7917	Intermediate Similarity	NPC253586
0.7912	Intermediate Similarity	NPC161928
0.7912	Intermediate Similarity	NPC210658
0.7912	Intermediate Similarity	NPC43912
0.7912	Intermediate Similarity	NPC5943
0.7912	Intermediate Similarity	NPC140446
0.7895	Intermediate Similarity	NPC21897
0.7879	Intermediate Similarity	NPC97260
0.7879	Intermediate Similarity	NPC476837
0.7879	Intermediate Similarity	NPC139181
0.7872	Intermediate Similarity	NPC167644
0.7872	Intermediate Similarity	NPC311246
0.7864	Intermediate Similarity	NPC272242
0.7849	Intermediate Similarity	NPC473542
0.7841	Intermediate Similarity	NPC58631
0.7841	Intermediate Similarity	NPC116320
0.7841	Intermediate Similarity	NPC119922
0.7826	Intermediate Similarity	NPC128475
0.7816	Intermediate Similarity	NPC31302
0.7816	Intermediate Similarity	NPC245029
0.7816	Intermediate Similarity	NPC80891
0.7816	Intermediate Similarity	NPC201276
0.7812	Intermediate Similarity	NPC296936
0.7802	Intermediate Similarity	NPC471411
0.7802	Intermediate Similarity	NPC92139
0.7802	Intermediate Similarity	NPC472272
0.7802	Intermediate Similarity	NPC64862
0.7802	Intermediate Similarity	NPC471410
0.78	Intermediate Similarity	NPC469827
0.7789	Intermediate Similarity	NPC3538
0.7789	Intermediate Similarity	NPC252253
0.7789	Intermediate Similarity	NPC477224
0.7789	Intermediate Similarity	NPC305418
0.7789	Intermediate Similarity	NPC113500
0.7789	Intermediate Similarity	NPC206878
0.7789	Intermediate Similarity	NPC45959
0.7789	Intermediate Similarity	NPC175
0.7778	Intermediate Similarity	NPC320824
0.7778	Intermediate Similarity	NPC65133
0.7766	Intermediate Similarity	NPC219516
0.7766	Intermediate Similarity	NPC149966
0.7766	Intermediate Similarity	NPC5632
0.7765	Intermediate Similarity	NPC317242
0.7765	Intermediate Similarity	NPC186851
0.7765	Intermediate Similarity	NPC243027
0.7765	Intermediate Similarity	NPC158208
0.7765	Intermediate Similarity	NPC196136
0.7755	Intermediate Similarity	NPC108371
0.7753	Intermediate Similarity	NPC477935
0.7753	Intermediate Similarity	NPC470611
0.7745	Intermediate Similarity	NPC469826
0.7742	Intermediate Similarity	NPC61688
0.7742	Intermediate Similarity	NPC131466
0.7742	Intermediate Similarity	NPC200580
0.7732	Intermediate Similarity	NPC472273
0.7732	Intermediate Similarity	NPC470591
0.7727	Intermediate Similarity	NPC261616
0.7727	Intermediate Similarity	NPC16449
0.7723	Intermediate Similarity	NPC166079
0.7723	Intermediate Similarity	NPC306776
0.7717	Intermediate Similarity	NPC45833
0.7717	Intermediate Similarity	NPC263802
0.7717	Intermediate Similarity	NPC202937
0.7717	Intermediate Similarity	NPC213658
0.7717	Intermediate Similarity	NPC62202
0.7717	Intermediate Similarity	NPC110365
0.7714	Intermediate Similarity	NPC102619
0.7708	Intermediate Similarity	NPC473065
0.7708	Intermediate Similarity	NPC473067
0.7708	Intermediate Similarity	NPC62407
0.7708	Intermediate Similarity	NPC473064
0.7708	Intermediate Similarity	NPC287354
0.7701	Intermediate Similarity	NPC191345
0.7701	Intermediate Similarity	NPC34046
0.7701	Intermediate Similarity	NPC171426
0.7701	Intermediate Similarity	NPC324700
0.7701	Intermediate Similarity	NPC252483
0.7701	Intermediate Similarity	NPC43463
0.7701	Intermediate Similarity	NPC80089
0.7701	Intermediate Similarity	NPC224802
0.7692	Intermediate Similarity	NPC290612
0.7684	Intermediate Similarity	NPC144790
0.7684	Intermediate Similarity	NPC476189
0.7684	Intermediate Similarity	NPC475307
0.7684	Intermediate Similarity	NPC149400
0.7684	Intermediate Similarity	NPC88962
0.7677	Intermediate Similarity	NPC178853
0.7677	Intermediate Similarity	NPC476838
0.7677	Intermediate Similarity	NPC476839
0.7674	Intermediate Similarity	NPC136424
0.7674	Intermediate Similarity	NPC163597
0.7667	Intermediate Similarity	NPC2572
0.7667	Intermediate Similarity	NPC69953
0.7667	Intermediate Similarity	NPC29342
0.766	Intermediate Similarity	NPC279329
0.766	Intermediate Similarity	NPC473269
0.7647	Intermediate Similarity	NPC192501
0.7647	Intermediate Similarity	NPC10476
0.7647	Intermediate Similarity	NPC228994
0.764	Intermediate Similarity	NPC211049
0.764	Intermediate Similarity	NPC12933
0.7634	Intermediate Similarity	NPC476435
0.7634	Intermediate Similarity	NPC476379
0.7634	Intermediate Similarity	NPC281004

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 NPC201607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	3646
0.2-0.3	3476
0.3-0.4	958
0.4-0.5	303
0.5-0.6	249
0.6-0.7	86
0.7-0.8	12
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
0.7701	Intermediate Similarity	NPD6115	Approved
0.7701	Intermediate Similarity	NPD6118	Approved
0.7701	Intermediate Similarity	NPD6114	Approved
0.7701	Intermediate Similarity	NPD6697	Approved
0.759	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD8171	Discontinued
0.7471	Intermediate Similarity	NPD6117	Approved
0.7282	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6928	Phase 2
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.699	Remote Similarity	NPD1700	Approved
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3702	Approved
0.6778	Remote Similarity	NPD3703	Phase 2
0.6757	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8033	Approved
0.6638	Remote Similarity	NPD8380	Approved
0.6638	Remote Similarity	NPD8296	Approved
0.6638	Remote Similarity	NPD8379	Approved
0.6638	Remote Similarity	NPD8335	Approved
0.6638	Remote Similarity	NPD8378	Approved
0.6629	Remote Similarity	NPD5777	Approved
0.6629	Remote Similarity	NPD6081	Approved
0.6609	Remote Similarity	NPD7516	Approved
0.6606	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD3669	Approved
0.6562	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6319	Approved
0.6529	Remote Similarity	NPD7319	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.65	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD7492	Approved
0.6437	Remote Similarity	NPD4224	Phase 2
0.6435	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7525	Registered
0.6417	Remote Similarity	NPD7507	Approved
0.6417	Remote Similarity	NPD6616	Approved
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD8418	Phase 2
0.6415	Remote Similarity	NPD7640	Approved
0.641	Remote Similarity	NPD6059	Approved
0.641	Remote Similarity	NPD6054	Approved
0.6396	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD371	Approved
0.6364	Remote Similarity	NPD7078	Approved
0.6348	Remote Similarity	NPD6940	Discontinued
0.6346	Remote Similarity	NPD7991	Discontinued
0.6333	Remote Similarity	NPD4245	Approved
0.6333	Remote Similarity	NPD4789	Approved
0.6333	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4244	Approved
0.6321	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6306	Remote Similarity	NPD7320	Approved
0.6303	Remote Similarity	NPD6370	Approved
0.6296	Remote Similarity	NPD7632	Discontinued
0.6293	Remote Similarity	NPD7115	Discovery
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6264	Remote Similarity	NPD4758	Discontinued
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6372	Approved
0.6222	Remote Similarity	NPD3698	Phase 2
0.6218	Remote Similarity	NPD6016	Approved
0.6218	Remote Similarity	NPD6015	Approved
0.6211	Remote Similarity	NPD5364	Discontinued
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4632	Approved
0.6167	Remote Similarity	NPD5988	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6649	Approved
0.6136	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6008	Approved
0.6116	Remote Similarity	NPD8328	Phase 3
0.6095	Remote Similarity	NPD7748	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.6083	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD7503	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6058	Remote Similarity	NPD7637	Suspended
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD4634	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6042	Remote Similarity	NPD3671	Phase 1
0.6036	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6847	Approved
0.598	Remote Similarity	NPD7524	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5957	Remote Similarity	NPD1810	Approved
0.5957	Remote Similarity	NPD1811	Approved
0.5934	Remote Similarity	NPD229	Approved
0.5929	Remote Similarity	NPD6412	Phase 2
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6084	Phase 2
0.5926	Remote Similarity	NPD6083	Phase 2
0.592	Remote Similarity	NPD6033	Approved
0.5888	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6009	Approved
0.5882	Remote Similarity	NPD8308	Discontinued
0.5877	Remote Similarity	NPD6686	Approved
0.5877	Remote Similarity	NPD6011	Approved
0.5877	Remote Similarity	NPD8174	Phase 2
0.5876	Remote Similarity	NPD4802	Phase 2
0.5876	Remote Similarity	NPD4238	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD1780	Approved
0.5859	Remote Similarity	NPD1779	Approved
0.5854	Remote Similarity	NPD7604	Phase 2
0.5842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5983	Phase 2
0.581	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6700	Approved
0.5806	Remote Similarity	NPD2686	Approved
0.5806	Remote Similarity	NPD2687	Approved
0.5806	Remote Similarity	NPD2254	Approved
0.5794	Remote Similarity	NPD7900	Approved
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4755	Approved
0.5763	Remote Similarity	NPD8298	Phase 2
0.576	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD6703	Approved
0.5755	Remote Similarity	NPD6702	Approved
0.5743	Remote Similarity	NPD6695	Phase 3
0.5743	Remote Similarity	NPD4788	Approved
0.5741	Remote Similarity	NPD5695	Phase 3
0.5727	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.5686	Remote Similarity	NPD4786	Approved
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4700	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.5673	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD6274	Approved
0.5667	Remote Similarity	NPD7909	Approved
0.5657	Remote Similarity	NPD7645	Phase 2
0.5656	Remote Similarity	NPD7100	Approved
0.5656	Remote Similarity	NPD7101	Approved
0.5652	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6079	Approved
0.5604	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6067	Discontinued

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