NPASS Compound

Structure

NPC208818 OpenBabel07101719402D 49 54 0 0 1 0 0 0 0 0999 V2000 3.4641 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5648 -6.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0077 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4454 -2.8397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1885 -3.5088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6987 0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2949 -1.6136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6550 0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2864 -4.1269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3663 -3.6011 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 8.9859 -0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4943 -3.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2730 -1.8215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7730 -2.6875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.9806 -4.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6331 -0.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0296 -4.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7206 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7512 -2.4796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9422 -1.0783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9541 -4.4101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7238 -5.1561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3023 0.6159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4115 1.6554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8216 -5.7742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 -0.0388 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 11.8557 -1.4851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 44 1 0 0 0 0 3 6 2 0 0 0 0 3 15 1 0 0 0 0 4 5 2 0 0 0 0 4 16 1 0 0 0 0 5 20 1 0 0 0 0 6 25 1 0 0 0 0 7 8 2 0 0 0 0 8 45 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 12 34 1 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 17 7 1 6 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 31 2 0 0 0 0 19 13 1 6 0 0 0 19 30 1 0 0 0 0 20 22 2 0 0 0 0 20 37 1 0 0 0 0 21 31 1 0 0 0 0 21 38 1 0 0 0 0 22 44 1 0 0 0 0 23 46 1 1 0 0 0 24 14 1 1 0 0 0 24 27 1 0 0 0 0 24 47 1 0 0 0 0 25 39 2 0 0 0 0 25 46 1 0 0 0 0 26 32 1 0 0 0 0 26 34 1 6 0 0 0 27 28 1 0 0 0 0 27 40 1 6 0 0 0 28 29 1 0 0 0 0 28 41 1 1 0 0 0 29 33 1 0 0 0 0 29 42 1 6 0 0 0 30 16 1 1 0 0 0 30 48 1 0 0 0 0 31 48 1 0 0 0 0 32 45 1 0 0 0 0 32 49 1 1 0 0 0 33 47 1 0 0 0 0 33 49 1 1 0 0 0 34 1 1 6 0 0 0 34 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	688.24
Volume:	653.406
LogP:	0.866
LogD:	0.728
LogS:	-4.383
# Rotatable Bonds:	10
TPSA:	234.29
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.131
Synthetic Accessibility Score:	5.451
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.3
MDCK Permeability:	6.667590059805661e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.83
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	78.92162322998047%
Volume Distribution (VD):	0.386
Pgp-substrate:	15.8596830368042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.588
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	1.392
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.328
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.114
Carcinogencity:	0.872
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.294

Download Data

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

Natural Product: NPC208818

Natural Product ID:	NPC208818
*Common Name:**	Rehmaglutoside E
IUPAC Name:	[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (E)-3-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate
Synonyms:	Rehmaglutoside E
Standard InCHIKey:	VZIRSMOIFOCIRI-WIYDDCBPSA-N
Standard InCHI:	InChI=1S/C34H40O15/c1-34(43)12-23(17-7-8-45-32(26(17)34)49-33-29(42)28(41)27(40)24(14-36)47-33)46-25(39)6-3-15-9-18-19(13-35)30(48-31(18)21(38)10-15)16-4-5-20(37)22(11-16)44-2/h3-11,17,19,23-24,26-30,32-33,35-38,40-43H,12-14H2,1-2H3/b6-3+/t17-,19+,23+,24+,26+,27+,28-,29+,30-,32-,33-,34-/m0/s1
SMILES:	C[C@@]1(C[C@H]([C@@H]2C=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC(=O)/C=C/c1cc2[C@@H](CO)[C@H](c3ccc(c(c3)OC)O)Oc2c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2177289
PubChem CID:	71457115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[568242]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[568242]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[568242]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[568242]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[568242]

☑ 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 NPC208818 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	383
0.1-0.2	1445
0.2-0.3	3257
0.3-0.4	7265
0.4-0.5	10061
0.5-0.6	6758
0.6-0.7	8873
0.7-0.8	4193
0.8-0.85	379
0.85-0.9	78
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9308	High Similarity	NPC478269
0.9193	High Similarity	NPC478267
0.913	High Similarity	NPC478265
0.9108	High Similarity	NPC269914
0.9108	High Similarity	NPC478249
0.9085	High Similarity	NPC475621
0.9062	High Similarity	NPC228357
0.9062	High Similarity	NPC11411
0.903	High Similarity	NPC286809
0.8944	High Similarity	NPC478248
0.8931	High Similarity	NPC478268
0.8924	High Similarity	NPC147224
0.8924	High Similarity	NPC98624
0.8917	High Similarity	NPC308178
0.8875	High Similarity	NPC478241
0.8875	High Similarity	NPC89693
0.8875	High Similarity	NPC229548
0.8862	High Similarity	NPC21956
0.8854	High Similarity	NPC31325
0.8854	High Similarity	NPC114505
0.8854	High Similarity	NPC213074
0.8854	High Similarity	NPC15956
0.8854	High Similarity	NPC193473
0.8854	High Similarity	NPC224674
0.8854	High Similarity	NPC275284
0.8841	High Similarity	NPC149873
0.8841	High Similarity	NPC7191
0.8827	High Similarity	NPC478266
0.8805	High Similarity	NPC188393
0.8805	High Similarity	NPC470934
0.8758	High Similarity	NPC115203
0.8726	High Similarity	NPC43508
0.8726	High Similarity	NPC163898
0.8726	High Similarity	NPC476301
0.872	High Similarity	NPC179914
0.872	High Similarity	NPC173726
0.872	High Similarity	NPC241600
0.8706	High Similarity	NPC316539
0.8696	High Similarity	NPC302610
0.8688	High Similarity	NPC475224
0.8671	High Similarity	NPC112861
0.8671	High Similarity	NPC199928
0.8662	High Similarity	NPC129417
0.8662	High Similarity	NPC79429
0.8662	High Similarity	NPC470235
0.8662	High Similarity	NPC471667
0.8662	High Similarity	NPC217635
0.8662	High Similarity	NPC283995
0.8662	High Similarity	NPC110063
0.8662	High Similarity	NPC232228
0.8642	High Similarity	NPC150442
0.8642	High Similarity	NPC469699
0.8631	High Similarity	NPC59516
0.8623	High Similarity	NPC109990
0.8608	High Similarity	NPC287615
0.8608	High Similarity	NPC216819
0.8608	High Similarity	NPC18979
0.8608	High Similarity	NPC22150
0.8608	High Similarity	NPC100998
0.8608	High Similarity	NPC262182
0.8608	High Similarity	NPC83743
0.8608	High Similarity	NPC38041
0.8608	High Similarity	NPC476382
0.8608	High Similarity	NPC34587
0.8608	High Similarity	NPC279298
0.8608	High Similarity	NPC252292
0.8608	High Similarity	NPC34927
0.8599	High Similarity	NPC185307
0.8599	High Similarity	NPC470950
0.8599	High Similarity	NPC46092
0.8599	High Similarity	NPC478239
0.858	High Similarity	NPC470264
0.858	High Similarity	NPC53587
0.858	High Similarity	NPC176186
0.858	High Similarity	NPC169404
0.8571	High Similarity	NPC472709
0.8571	High Similarity	NPC472710
0.8563	High Similarity	NPC145847
0.8562	High Similarity	NPC261122
0.8562	High Similarity	NPC28651
0.8562	High Similarity	NPC192763
0.8562	High Similarity	NPC300262
0.8562	High Similarity	NPC3460
0.8562	High Similarity	NPC210611
0.8562	High Similarity	NPC201148
0.8562	High Similarity	NPC199311
0.8562	High Similarity	NPC80732
0.8562	High Similarity	NPC215095
0.8553	High Similarity	NPC476865
0.8545	High Similarity	NPC125495
0.8544	High Similarity	NPC84181
0.8544	High Similarity	NPC292443
0.8535	High Similarity	NPC476356
0.8535	High Similarity	NPC157816
0.8535	High Similarity	NPC131971
0.8535	High Similarity	NPC140502
0.8535	High Similarity	NPC253878
0.8528	High Similarity	NPC245615
0.8528	High Similarity	NPC299706
0.8528	High Similarity	NPC61604
0.8528	High Similarity	NPC115466
0.8509	High Similarity	NPC471062
0.8509	High Similarity	NPC106138
0.8509	High Similarity	NPC44452
0.8509	High Similarity	NPC473427
0.8509	High Similarity	NPC306890
0.8509	High Similarity	NPC259347
0.8509	High Similarity	NPC94871
0.8509	High Similarity	NPC476398
0.8509	High Similarity	NPC470933
0.8509	High Similarity	NPC476386
0.85	High Similarity	NPC18789
0.85	High Similarity	NPC232992
0.8491	Intermediate Similarity	NPC476869
0.8491	Intermediate Similarity	NPC476864
0.8491	Intermediate Similarity	NPC476868
0.8491	Intermediate Similarity	NPC476866
0.8485	Intermediate Similarity	NPC163635
0.8481	Intermediate Similarity	NPC302286
0.8481	Intermediate Similarity	NPC477898
0.8481	Intermediate Similarity	NPC116104
0.8481	Intermediate Similarity	NPC237872
0.8481	Intermediate Similarity	NPC263397
0.8481	Intermediate Similarity	NPC88754
0.8476	Intermediate Similarity	NPC159922
0.8471	Intermediate Similarity	NPC186406
0.8471	Intermediate Similarity	NPC471414
0.8471	Intermediate Similarity	NPC472711
0.8457	Intermediate Similarity	NPC257970
0.8457	Intermediate Similarity	NPC476871
0.8457	Intermediate Similarity	NPC470927
0.8452	Intermediate Similarity	NPC476011
0.8447	Intermediate Similarity	NPC474940
0.8447	Intermediate Similarity	NPC474795
0.8447	Intermediate Similarity	NPC270751
0.8447	Intermediate Similarity	NPC303013
0.8447	Intermediate Similarity	NPC236166
0.8447	Intermediate Similarity	NPC159697
0.8447	Intermediate Similarity	NPC130959
0.8438	Intermediate Similarity	NPC37838
0.8438	Intermediate Similarity	NPC205796
0.8438	Intermediate Similarity	NPC276753
0.8438	Intermediate Similarity	NPC474234
0.8428	Intermediate Similarity	NPC300894
0.8428	Intermediate Similarity	NPC474444
0.8428	Intermediate Similarity	NPC296954
0.8428	Intermediate Similarity	NPC196063
0.8428	Intermediate Similarity	NPC141455
0.8428	Intermediate Similarity	NPC284881
0.8428	Intermediate Similarity	NPC476867
0.8428	Intermediate Similarity	NPC471063
0.8428	Intermediate Similarity	NPC264706
0.8428	Intermediate Similarity	NPC93433
0.8418	Intermediate Similarity	NPC246947
0.8412	Intermediate Similarity	NPC282551
0.8405	Intermediate Similarity	NPC125823
0.8405	Intermediate Similarity	NPC143480
0.8405	Intermediate Similarity	NPC7145
0.8405	Intermediate Similarity	NPC85192
0.8395	Intermediate Similarity	NPC181452
0.8395	Intermediate Similarity	NPC51328
0.8395	Intermediate Similarity	NPC286235
0.8395	Intermediate Similarity	NPC220006
0.8395	Intermediate Similarity	NPC90896
0.8395	Intermediate Similarity	NPC283839
0.8395	Intermediate Similarity	NPC475940
0.8395	Intermediate Similarity	NPC474893
0.8395	Intermediate Similarity	NPC55158
0.8385	Intermediate Similarity	NPC39657
0.8385	Intermediate Similarity	NPC97240
0.8375	Intermediate Similarity	NPC469586
0.8373	Intermediate Similarity	NPC189730
0.8373	Intermediate Similarity	NPC478055
0.8365	Intermediate Similarity	NPC113680
0.8365	Intermediate Similarity	NPC278961
0.8365	Intermediate Similarity	NPC40305
0.8365	Intermediate Similarity	NPC105005
0.8354	Intermediate Similarity	NPC289967
0.8354	Intermediate Similarity	NPC215060
0.8354	Intermediate Similarity	NPC476352
0.8354	Intermediate Similarity	NPC472612
0.8354	Intermediate Similarity	NPC203664
0.8354	Intermediate Similarity	NPC472611
0.8344	Intermediate Similarity	NPC328273
0.8344	Intermediate Similarity	NPC100389
0.8344	Intermediate Similarity	NPC321184
0.8344	Intermediate Similarity	NPC321638
0.8344	Intermediate Similarity	NPC158635
0.8344	Intermediate Similarity	NPC229882
0.8344	Intermediate Similarity	NPC226005
0.8344	Intermediate Similarity	NPC171134
0.8343	Intermediate Similarity	NPC12326
0.8333	Intermediate Similarity	NPC93924
0.8333	Intermediate Similarity	NPC474856
0.8333	Intermediate Similarity	NPC474834
0.8333	Intermediate Similarity	NPC193377
0.8333	Intermediate Similarity	NPC130449
0.8333	Intermediate Similarity	NPC169510
0.8333	Intermediate Similarity	NPC476348
0.8333	Intermediate Similarity	NPC304048

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 NPC208818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	846
0.2-0.3	1816
0.3-0.4	2717
0.4-0.5	1940
0.5-0.6	1030
0.6-0.7	427
0.7-0.8	69
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD7685	Pre-registration
0.8228	Intermediate Similarity	NPD7266	Discontinued
0.8192	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1653	Approved
0.8046	Intermediate Similarity	NPD7228	Approved
0.7965	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD6674	Discontinued
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7841	Intermediate Similarity	NPD3818	Discontinued
0.7797	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8127	Discontinued
0.7753	Intermediate Similarity	NPD7472	Approved
0.7753	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD4966	Approved
0.7733	Intermediate Similarity	NPD4967	Phase 2
0.7733	Intermediate Similarity	NPD4965	Approved
0.7719	Intermediate Similarity	NPD8455	Phase 2
0.7669	Intermediate Similarity	NPD5763	Approved
0.7669	Intermediate Similarity	NPD5762	Approved
0.7661	Intermediate Similarity	NPD37	Approved
0.7624	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7808	Phase 3
0.7582	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD7251	Discontinued
0.7569	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6005	Phase 3
0.7455	Intermediate Similarity	NPD6004	Phase 3
0.7455	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6002	Phase 3
0.7442	Intermediate Similarity	NPD7028	Phase 2
0.7421	Intermediate Similarity	NPD2861	Phase 2
0.7407	Intermediate Similarity	NPD4060	Phase 1
0.7403	Intermediate Similarity	NPD5844	Phase 1
0.738	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5124	Phase 1
0.7362	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3027	Phase 3
0.7317	Intermediate Similarity	NPD6653	Approved
0.7314	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3620	Phase 2
0.7301	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD7097	Phase 1
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1934	Approved
0.7254	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6166	Phase 2
0.7235	Intermediate Similarity	NPD5058	Phase 3
0.7228	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5494	Approved
0.7205	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4140	Approved
0.7191	Intermediate Similarity	NPD7075	Discontinued
0.7178	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD5735	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7119	Intermediate Similarity	NPD1465	Phase 2
0.7119	Intermediate Similarity	NPD7819	Suspended
0.711	Intermediate Similarity	NPD6273	Approved
0.7079	Intermediate Similarity	NPD3817	Phase 2
0.7076	Intermediate Similarity	NPD6190	Approved
0.7069	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3705	Approved
0.7039	Intermediate Similarity	NPD3882	Suspended
0.7024	Intermediate Similarity	NPD7033	Discontinued
0.7022	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2801	Approved
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD7473	Discontinued
0.701	Intermediate Similarity	NPD7930	Approved
0.6989	Remote Similarity	NPD7458	Discontinued
0.6984	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6801	Discontinued
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7768	Phase 2
0.694	Remote Similarity	NPD6232	Discontinued
0.6919	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4110	Phase 3
0.6919	Remote Similarity	NPD8166	Discontinued
0.6914	Remote Similarity	NPD8651	Approved
0.6914	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8434	Phase 2
0.6909	Remote Similarity	NPD7095	Approved
0.6905	Remote Similarity	NPD6353	Approved
0.6901	Remote Similarity	NPD2424	Discontinued
0.6893	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD7799	Discontinued
0.6882	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD6842	Approved
0.6875	Remote Similarity	NPD7906	Approved
0.6875	Remote Similarity	NPD6841	Approved
0.6875	Remote Similarity	NPD6843	Phase 3
0.6867	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7783	Phase 2
0.6863	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1357	Approved
0.685	Remote Similarity	NPD7435	Discontinued
0.6842	Remote Similarity	NPD7313	Approved
0.6842	Remote Similarity	NPD7312	Approved
0.6842	Remote Similarity	NPD7310	Approved
0.6842	Remote Similarity	NPD7311	Approved
0.6833	Remote Similarity	NPD5760	Phase 2
0.6833	Remote Similarity	NPD5761	Phase 2
0.6832	Remote Similarity	NPD1610	Phase 2
0.6824	Remote Similarity	NPD5588	Approved
0.6821	Remote Similarity	NPD3750	Approved
0.6821	Remote Similarity	NPD6331	Phase 2
0.6816	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4625	Phase 3
0.6806	Remote Similarity	NPD7309	Approved
0.68	Remote Similarity	NPD1511	Approved
0.6798	Remote Similarity	NPD7585	Approved
0.6784	Remote Similarity	NPD2935	Discontinued
0.6782	Remote Similarity	NPD7999	Approved
0.678	Remote Similarity	NPD5403	Approved
0.6774	Remote Similarity	NPD2489	Approved
0.6774	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD27	Approved
0.6768	Remote Similarity	NPD2797	Approved
0.6768	Remote Similarity	NPD6362	Approved
0.6768	Remote Similarity	NPD3094	Phase 2
0.6766	Remote Similarity	NPD6798	Discontinued
0.6765	Remote Similarity	NPD4538	Approved
0.6765	Remote Similarity	NPD8151	Discontinued
0.6765	Remote Similarity	NPD4536	Approved
0.6765	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3787	Discontinued
0.6749	Remote Similarity	NPD7583	Approved
0.6748	Remote Similarity	NPD5327	Phase 3
0.6746	Remote Similarity	NPD1933	Approved
0.6746	Remote Similarity	NPD4340	Discontinued
0.6743	Remote Similarity	NPD6666	Approved
0.6743	Remote Similarity	NPD6667	Approved
0.674	Remote Similarity	NPD2977	Approved
0.674	Remote Similarity	NPD2978	Approved
0.6736	Remote Similarity	NPD8150	Discontinued
0.6736	Remote Similarity	NPD4663	Approved
0.6732	Remote Similarity	NPD7874	Approved
0.6732	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD422	Phase 1
0.6727	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1512	Approved
0.6722	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2969	Approved
0.672	Remote Similarity	NPD2970	Approved
0.6716	Remote Similarity	NPD6823	Phase 2
0.6708	Remote Similarity	NPD4626	Approved
0.6708	Remote Similarity	NPD5125	Phase 3
0.6708	Remote Similarity	NPD5126	Approved
0.67	Remote Similarity	NPD6780	Approved
0.67	Remote Similarity	NPD6781	Approved
0.67	Remote Similarity	NPD6777	Approved
0.67	Remote Similarity	NPD6782	Approved
0.67	Remote Similarity	NPD6776	Approved
0.67	Remote Similarity	NPD6778	Approved
0.67	Remote Similarity	NPD6779	Approved
0.6688	Remote Similarity	NPD5283	Phase 1
0.6687	Remote Similarity	NPD5736	Approved
0.6685	Remote Similarity	NPD919	Approved
0.6684	Remote Similarity	NPD4481	Phase 3
0.6683	Remote Similarity	NPD7696	Phase 3
0.6683	Remote Similarity	NPD7697	Approved
0.6683	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7985	Registered
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD3051	Approved
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4578	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD5401	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