NPASS Compound

Structure

NPC476114 OpenBabel07101719252D 37 41 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 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 -8.4145 3.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0023 3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4200 3.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5955 2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 3 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 -7.6010 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 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 -6.0622 1.5000 0.0000 C 0 0 0 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 -5.1962 -2.0000 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 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 N 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 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 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 0.0000 -0.0000 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 1 2 2 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 27 1 0 0 0 0 9 15 1 0 0 0 0 10 29 1 0 0 0 0 11 16 2 0 0 0 0 11 35 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 16 24 1 0 0 0 0 17 28 1 0 0 0 0 18 9 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 10 1 6 0 0 0 19 21 1 0 0 0 0 19 36 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 25 37 1 6 0 0 0 26 36 1 0 0 0 0 26 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.21
Volume:	498.12
LogP:	-0.749
LogD:	0.482
LogS:	-1.986
# Rotatable Bonds:	7
TPSA:	173.73
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	4.863
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
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:	-6.2
MDCK Permeability:	1.484099448134657e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.705
Human Intestinal Absorption (HIA):	0.934
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	54.7022819519043%
Volume Distribution (VD):	0.482
Pgp-substrate:	54.542320251464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	1.208
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.225
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.673
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.063
Carcinogencity:	0.924
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC476114

Natural Product ID:	NPC476114
*Common Name:**	Strictosidinic Acid
IUPAC Name:	(2S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
Synonyms:	strictosidinic acid
Standard InCHIKey:	CMMIVMFGFIBAGC-IEUFSHIYSA-N
Standard InCHI:	InChI=1S/C26H32N2O9/c1-2-12-15(9-18-20-14(7-8-27-18)13-5-3-4-6-17(13)28-20)16(24(33)34)11-35-25(12)37-26-23(32)22(31)21(30)19(10-29)36-26/h2-6,11-12,15,18-19,21-23,25-32H,1,7-10H2,(H,33,34)/t12?,15?,18-,19+,21+,22-,23+,25-,26-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(C2C=C)C[C@@H]2NCCc3c2[nH]c2c3cccc2)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL528546
PubChem CID:	44575750
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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	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	4

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[559016]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	80000.0	nM	PMID[559016]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	80000.0	nM	PMID[559016]
NPT1	Others	Radical scavenging activity		IC50	=	49700.0	nM	PMID[559015]

☑ 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 NPC476114 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	270
0.1-0.2	1264
0.2-0.3	4917
0.3-0.4	16904
0.4-0.5	13563
0.5-0.6	3467
0.6-0.7	1899
0.7-0.8	347
0.8-0.85	39
0.85-0.9	10
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC82070
0.9548	High Similarity	NPC475271
0.9444	High Similarity	NPC52254
0.9296	High Similarity	NPC174788
0.9223	High Similarity	NPC476115
0.9082	High Similarity	NPC474905
0.8645	High Similarity	NPC57453
0.8586	High Similarity	NPC294909
0.8586	High Similarity	NPC254240
0.8586	High Similarity	NPC128265
0.8586	High Similarity	NPC312870
0.8586	High Similarity	NPC199851
0.8341	Intermediate Similarity	NPC477548
0.8265	Intermediate Similarity	NPC111602
0.8265	Intermediate Similarity	NPC175474
0.8265	Intermediate Similarity	NPC63199
0.8265	Intermediate Similarity	NPC102338
0.8265	Intermediate Similarity	NPC196251
0.823	Intermediate Similarity	NPC313640
0.8223	Intermediate Similarity	NPC472112
0.8186	Intermediate Similarity	NPC473800
0.8141	Intermediate Similarity	NPC472113
0.8128	Intermediate Similarity	NPC313985
0.8128	Intermediate Similarity	NPC49196
0.8128	Intermediate Similarity	NPC79129
0.8128	Intermediate Similarity	NPC249150
0.8128	Intermediate Similarity	NPC195461
0.8128	Intermediate Similarity	NPC81654
0.8119	Intermediate Similarity	NPC50503
0.803	Intermediate Similarity	NPC52557
0.8009	Intermediate Similarity	NPC221100
0.8009	Intermediate Similarity	NPC234078
0.799	Intermediate Similarity	NPC50997
0.799	Intermediate Similarity	NPC160127
0.797	Intermediate Similarity	NPC19692
0.797	Intermediate Similarity	NPC220151
0.795	Intermediate Similarity	NPC469470
0.795	Intermediate Similarity	NPC469501
0.7931	Intermediate Similarity	NPC245916
0.7919	Intermediate Similarity	NPC139291
0.7919	Intermediate Similarity	NPC472108
0.789	Intermediate Similarity	NPC21638
0.7864	Intermediate Similarity	NPC33949
0.7822	Intermediate Similarity	NPC472097
0.7806	Intermediate Similarity	NPC183662
0.7806	Intermediate Similarity	NPC15573
0.7806	Intermediate Similarity	NPC217372
0.7789	Intermediate Similarity	NPC258480
0.7778	Intermediate Similarity	NPC281049
0.7766	Intermediate Similarity	NPC219336
0.7761	Intermediate Similarity	NPC472323
0.7739	Intermediate Similarity	NPC472109
0.7739	Intermediate Similarity	NPC472110
0.7727	Intermediate Similarity	NPC469896
0.7711	Intermediate Similarity	NPC66210
0.7678	Intermediate Similarity	NPC238457
0.7674	Intermediate Similarity	NPC229348
0.765	Intermediate Similarity	NPC249428
0.7638	Intermediate Similarity	NPC15840
0.7619	Intermediate Similarity	NPC476874
0.7613	Intermediate Similarity	NPC472762
0.7604	Intermediate Similarity	NPC148183
0.7604	Intermediate Similarity	NPC152768
0.76	Intermediate Similarity	NPC71037
0.759	Intermediate Similarity	NPC317430
0.7569	Intermediate Similarity	NPC312645
0.7559	Intermediate Similarity	NPC244741
0.7546	Intermediate Similarity	NPC111732
0.7537	Intermediate Similarity	NPC315555
0.7537	Intermediate Similarity	NPC235684
0.7536	Intermediate Similarity	NPC289299
0.7536	Intermediate Similarity	NPC20593
0.7536	Intermediate Similarity	NPC57994
0.7535	Intermediate Similarity	NPC234999
0.7522	Intermediate Similarity	NPC89987
0.7512	Intermediate Similarity	NPC113626
0.7512	Intermediate Similarity	NPC472291
0.7512	Intermediate Similarity	NPC18661
0.7488	Intermediate Similarity	NPC79062
0.7488	Intermediate Similarity	NPC469743
0.7488	Intermediate Similarity	NPC472107
0.7487	Intermediate Similarity	NPC472122
0.7487	Intermediate Similarity	NPC24594
0.7476	Intermediate Similarity	NPC241024
0.7475	Intermediate Similarity	NPC322043
0.7475	Intermediate Similarity	NPC472123
0.7475	Intermediate Similarity	NPC327373
0.7475	Intermediate Similarity	NPC325093
0.7466	Intermediate Similarity	NPC472099
0.7465	Intermediate Similarity	NPC475778
0.7463	Intermediate Similarity	NPC182814
0.7453	Intermediate Similarity	NPC474116
0.745	Intermediate Similarity	NPC326575
0.7441	Intermediate Similarity	NPC214428
0.744	Intermediate Similarity	NPC55493
0.7438	Intermediate Similarity	NPC472119
0.7431	Intermediate Similarity	NPC89508
0.7427	Intermediate Similarity	NPC314333
0.7418	Intermediate Similarity	NPC476098
0.7418	Intermediate Similarity	NPC165599
0.7417	Intermediate Similarity	NPC191489
0.7415	Intermediate Similarity	NPC328798
0.7415	Intermediate Similarity	NPC325775
0.7412	Intermediate Similarity	NPC473105
0.7407	Intermediate Similarity	NPC478158
0.7404	Intermediate Similarity	NPC472295
0.7404	Intermediate Similarity	NPC269886
0.7404	Intermediate Similarity	NPC472210
0.7404	Intermediate Similarity	NPC81802
0.7404	Intermediate Similarity	NPC247735
0.7402	Intermediate Similarity	NPC318020
0.7397	Intermediate Similarity	NPC478157
0.7391	Intermediate Similarity	NPC127647
0.7389	Intermediate Similarity	NPC472444
0.7389	Intermediate Similarity	NPC472104
0.7389	Intermediate Similarity	NPC469358
0.7389	Intermediate Similarity	NPC143533
0.7385	Intermediate Similarity	NPC244856
0.7385	Intermediate Similarity	NPC151976
0.7379	Intermediate Similarity	NPC46413
0.7376	Intermediate Similarity	NPC472105
0.7376	Intermediate Similarity	NPC187827
0.7375	Intermediate Similarity	NPC284685
0.7371	Intermediate Similarity	NPC162730
0.7368	Intermediate Similarity	NPC475720
0.7368	Intermediate Similarity	NPC474192
0.7366	Intermediate Similarity	NPC62749
0.7366	Intermediate Similarity	NPC64216
0.7363	Intermediate Similarity	NPC234987
0.7354	Intermediate Similarity	NPC2395
0.7347	Intermediate Similarity	NPC21174
0.7347	Intermediate Similarity	NPC271797
0.7344	Intermediate Similarity	NPC472846
0.7343	Intermediate Similarity	NPC329858
0.7318	Intermediate Similarity	NPC274842
0.7315	Intermediate Similarity	NPC46225
0.7306	Intermediate Similarity	NPC207020
0.7295	Intermediate Similarity	NPC315634
0.7295	Intermediate Similarity	NPC88923
0.7295	Intermediate Similarity	NPC100734
0.7293	Intermediate Similarity	NPC54803
0.7293	Intermediate Similarity	NPC321592
0.7285	Intermediate Similarity	NPC204491
0.7282	Intermediate Similarity	NPC478077
0.7281	Intermediate Similarity	NPC127677
0.7277	Intermediate Similarity	NPC111275
0.7273	Intermediate Similarity	NPC236424
0.7273	Intermediate Similarity	NPC54744
0.7273	Intermediate Similarity	NPC306644
0.7269	Intermediate Similarity	NPC277350
0.7269	Intermediate Similarity	NPC57690
0.7264	Intermediate Similarity	NPC189812
0.7264	Intermediate Similarity	NPC203468
0.7264	Intermediate Similarity	NPC149155
0.7264	Intermediate Similarity	NPC329688
0.7264	Intermediate Similarity	NPC110500
0.7257	Intermediate Similarity	NPC141428
0.7257	Intermediate Similarity	NPC235885
0.7253	Intermediate Similarity	NPC475816
0.7251	Intermediate Similarity	NPC231342
0.7251	Intermediate Similarity	NPC472293
0.7248	Intermediate Similarity	NPC162860
0.7241	Intermediate Similarity	NPC472443
0.7241	Intermediate Similarity	NPC283219
0.7236	Intermediate Similarity	NPC78020
0.7235	Intermediate Similarity	NPC88008
0.7233	Intermediate Similarity	NPC133591
0.723	Intermediate Similarity	NPC472296
0.723	Intermediate Similarity	NPC472297
0.7228	Intermediate Similarity	NPC267885
0.7227	Intermediate Similarity	NPC87856
0.7227	Intermediate Similarity	NPC75634
0.7227	Intermediate Similarity	NPC476516
0.7225	Intermediate Similarity	NPC24370
0.7225	Intermediate Similarity	NPC319232
0.7217	Intermediate Similarity	NPC141454
0.7209	Intermediate Similarity	NPC193761
0.7207	Intermediate Similarity	NPC330009
0.7207	Intermediate Similarity	NPC74969
0.7207	Intermediate Similarity	NPC469928
0.7206	Intermediate Similarity	NPC91179
0.7205	Intermediate Similarity	NPC223409
0.7205	Intermediate Similarity	NPC95240
0.7205	Intermediate Similarity	NPC322135
0.7204	Intermediate Similarity	NPC202812
0.7198	Intermediate Similarity	NPC291759
0.7196	Intermediate Similarity	NPC249040
0.7195	Intermediate Similarity	NPC267965
0.7195	Intermediate Similarity	NPC315467
0.719	Intermediate Similarity	NPC476514
0.719	Intermediate Similarity	NPC472292
0.7186	Intermediate Similarity	NPC284888
0.7186	Intermediate Similarity	NPC323752
0.7183	Intermediate Similarity	NPC149708
0.7183	Intermediate Similarity	NPC102008
0.7183	Intermediate Similarity	NPC470499
0.7183	Intermediate Similarity	NPC306376
0.7178	Intermediate Similarity	NPC472586
0.7176	Intermediate Similarity	NPC98715
0.7175	Intermediate Similarity	NPC472285

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 NPC476114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	458
0.2-0.3	651
0.3-0.4	1705
0.4-0.5	3097
0.5-0.6	2386
0.6-0.7	617
0.7-0.8	57
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8586	High Similarity	NPD4500	Approved
0.8586	High Similarity	NPD4501	Approved
0.8128	Intermediate Similarity	NPD4600	Approved
0.8128	Intermediate Similarity	NPD4601	Approved
0.7556	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4602	Approved
0.7489	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD8325	Phase 3
0.7489	Intermediate Similarity	NPD8326	Phase 3
0.7476	Intermediate Similarity	NPD6248	Phase 2
0.7476	Intermediate Similarity	NPD6249	Phase 2
0.7475	Intermediate Similarity	NPD2092	Phase 2
0.7475	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD2095	Phase 2
0.7475	Intermediate Similarity	NPD2094	Phase 2
0.7465	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2096	Phase 2
0.7438	Intermediate Similarity	NPD2091	Phase 2
0.743	Intermediate Similarity	NPD7957	Phase 1
0.743	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4499	Approved
0.7417	Intermediate Similarity	NPD7708	Approved
0.7407	Intermediate Similarity	NPD4506	Discontinued
0.7375	Intermediate Similarity	NPD7955	Approved
0.7375	Intermediate Similarity	NPD7956	Approved
0.7302	Intermediate Similarity	NPD5901	Discontinued
0.7299	Intermediate Similarity	NPD5003	Discontinued
0.7295	Intermediate Similarity	NPD7803	Approved
0.7294	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD482	Approved
0.724	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2844	Phase 3
0.7227	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4885	Approved
0.7206	Intermediate Similarity	NPD5897	Approved
0.7206	Intermediate Similarity	NPD5898	Approved
0.7206	Intermediate Similarity	NPD5899	Approved
0.7188	Intermediate Similarity	NPD6770	Approved
0.7183	Intermediate Similarity	NPD7777	Approved
0.7183	Intermediate Similarity	NPD7778	Approved
0.7183	Intermediate Similarity	NPD53	Approved
0.7176	Intermediate Similarity	NPD5487	Phase 1
0.7176	Intermediate Similarity	NPD8072	Approved
0.7163	Intermediate Similarity	NPD7727	Phase 2
0.715	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3393	Approved
0.713	Intermediate Similarity	NPD3394	Approved
0.713	Intermediate Similarity	NPD3389	Approved
0.7129	Intermediate Similarity	NPD43	Approved
0.7129	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6182	Approved
0.7129	Intermediate Similarity	NPD4334	Discontinued
0.7123	Intermediate Similarity	NPD8423	Phase 2
0.7123	Intermediate Similarity	NPD8399	Phase 1
0.7104	Intermediate Similarity	NPD7470	Discontinued
0.7091	Intermediate Similarity	NPD4520	Approved
0.7067	Intermediate Similarity	NPD7878	Phase 2
0.7064	Intermediate Similarity	NPD8115	Approved
0.7064	Intermediate Similarity	NPD8114	Approved
0.7056	Intermediate Similarity	NPD6206	Phase 1
0.7051	Intermediate Similarity	NPD8073	Approved
0.7045	Intermediate Similarity	NPD2510	Approved
0.7045	Intermediate Similarity	NPD2509	Approved
0.7032	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6261	Phase 3
0.7014	Intermediate Similarity	NPD2564	Approved
0.7014	Intermediate Similarity	NPD2565	Phase 2
0.6995	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7234	Approved
0.6967	Remote Similarity	NPD7233	Approved
0.6964	Remote Similarity	NPD3794	Approved
0.6964	Remote Similarity	NPD3795	Approved
0.6961	Remote Similarity	NPD750	Phase 2
0.6959	Remote Similarity	NPD484	Approved
0.6948	Remote Similarity	NPD4315	Phase 2
0.6944	Remote Similarity	NPD4397	Phase 1
0.6942	Remote Similarity	NPD6642	Approved
0.6942	Remote Similarity	NPD6641	Approved
0.6941	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7817	Phase 1
0.6923	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5632	Approved
0.691	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5426	Phase 3
0.6897	Remote Similarity	NPD7730	Approved
0.6897	Remote Similarity	NPD7731	Approved
0.6894	Remote Similarity	NPD7950	Approved
0.6894	Remote Similarity	NPD7789	Approved
0.6894	Remote Similarity	NPD7953	Approved
0.6894	Remote Similarity	NPD7790	Approved
0.6894	Remote Similarity	NPD7791	Approved
0.6894	Remote Similarity	NPD7951	Approved
0.6894	Remote Similarity	NPD7952	Approved
0.6892	Remote Similarity	NPD2916	Discontinued
0.6888	Remote Similarity	NPD8468	Phase 2
0.6884	Remote Similarity	NPD7944	Discontinued
0.6883	Remote Similarity	NPD7271	Approved
0.6878	Remote Similarity	NPD3003	Approved
0.6872	Remote Similarity	NPD5444	Phase 1
0.6867	Remote Similarity	NPD7781	Approved
0.6867	Remote Similarity	NPD7780	Approved
0.6864	Remote Similarity	NPD6176	Phase 1
0.6863	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1326	Approved
0.6863	Remote Similarity	NPD1325	Approved
0.6861	Remote Similarity	NPD5835	Phase 3
0.6861	Remote Similarity	NPD5834	Phase 3
0.6861	Remote Similarity	NPD6529	Discontinued
0.6858	Remote Similarity	NPD4897	Phase 2
0.6857	Remote Similarity	NPD6178	Phase 3
0.6849	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5065	Approved
0.6842	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8374	Phase 3
0.6838	Remote Similarity	NPD7824	Approved
0.6835	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8283	Approved
0.6833	Remote Similarity	NPD8282	Approved
0.6833	Remote Similarity	NPD8272	Phase 2
0.6833	Remote Similarity	NPD56	Approved
0.6833	Remote Similarity	NPD8098	Approved
0.6825	Remote Similarity	NPD5075	Discontinued
0.6822	Remote Similarity	NPD7558	Phase 2
0.6812	Remote Similarity	NPD2382	Approved
0.6812	Remote Similarity	NPD2380	Approved
0.6812	Remote Similarity	NPD2381	Approved
0.6812	Remote Similarity	NPD5104	Approved
0.6812	Remote Similarity	NPD7194	Discontinued
0.681	Remote Similarity	NPD5596	Phase 2
0.6808	Remote Similarity	NPD1534	Approved
0.6804	Remote Similarity	NPD6479	Discontinued
0.6803	Remote Similarity	NPD5482	Discontinued
0.68	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5473	Discontinued
0.6793	Remote Similarity	NPD8329	Phase 3
0.6791	Remote Similarity	NPD6665	Discontinued
0.6789	Remote Similarity	NPD7946	Pre-registration
0.6789	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8370	Discontinued
0.677	Remote Similarity	NPD8465	Approved
0.677	Remote Similarity	NPD8467	Approved
0.677	Remote Similarity	NPD8466	Approved
0.6767	Remote Similarity	NPD7716	Approved
0.6767	Remote Similarity	NPD7717	Approved
0.6763	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4948	Discontinued
0.6758	Remote Similarity	NPD1768	Approved
0.6756	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD8321	Discontinued
0.6752	Remote Similarity	NPD6164	Phase 2
0.6752	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4086	Phase 1
0.6752	Remote Similarity	NPD6165	Phase 2
0.6741	Remote Similarity	NPD7665	Phase 2
0.6741	Remote Similarity	NPD7666	Phase 3
0.6732	Remote Similarity	NPD8364	Approved
0.6732	Remote Similarity	NPD8363	Approved
0.6728	Remote Similarity	NPD4427	Phase 2
0.6728	Remote Similarity	NPD7619	Phase 3
0.6728	Remote Similarity	NPD7618	Phase 3
0.6724	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6531	Approved
0.672	Remote Similarity	NPD6530	Approved
0.6718	Remote Similarity	NPD7181	Phase 3
0.6716	Remote Similarity	NPD2915	Discontinued
0.6714	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2920	Discontinued
0.6712	Remote Similarity	NPD3777	Phase 3
0.6711	Remote Similarity	NPD5902	Approved
0.6711	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5903	Approved
0.6711	Remote Similarity	NPD7970	Approved
0.671	Remote Similarity	NPD3280	Approved
0.6709	Remote Similarity	NPD7797	Approved
0.6709	Remote Similarity	NPD7603	Discontinued
0.6709	Remote Similarity	NPD7796	Approved
0.6709	Remote Similarity	NPD8289	Discontinued
0.6708	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2144	Approved
0.6699	Remote Similarity	NPD7865	Approved
0.6696	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6716	Phase 1
0.6683	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3038	Discontinued
0.6682	Remote Similarity	NPD7000	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