NPASS Compound

Structure

NPC475271 OpenBabel07101719522D 41 45 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 -6.0622 -3.5000 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 -0.0000 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 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 -4.3301 -0.5000 0.0000 C 0 0 3 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 -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 -4.3301 2.5000 0.0000 C 0 0 3 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 -3.4641 3.0000 0.0000 C 0 0 0 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 3 2 0 0 0 0 2 38 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 17 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 31 1 0 0 0 0 11 16 2 0 0 0 0 11 39 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 15 21 2 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 8 1 1 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 10 1 6 0 0 0 20 22 1 0 0 0 0 20 40 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 28 1 0 0 0 0 24 34 1 1 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 37 2 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 27 41 1 6 0 0 0 28 40 1 0 0 0 0 28 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.22
Volume:	547.656
LogP:	-0.226
LogD:	0.715
LogS:	-2.089
# Rotatable Bonds:	9
TPSA:	200.03
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	5.031
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:	-6.348
MDCK Permeability:	3.720141830854118e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.254
Human Intestinal Absorption (HIA):	0.944
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	50.26145553588867%
Volume Distribution (VD):	0.339
Pgp-substrate:	38.81846237182617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.219
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.109

ADMET: Excretion

Clearance (CL):	1.225
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.722
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.085
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475271

Natural Product ID:	NPC475271
*Common Name:**	5 Alpha-Carboxystrictosidine
IUPAC Name:	(1S)-1-[[(2S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:	5 Alpha-Carboxystrictosidine
Standard InCHIKey:	LHKZIVMTXZLOTP-VBWBPHJZSA-N
Standard InCHI:	InChI=1S/C28H34N2O11/c1-3-12-14(8-18-21-15(9-19(29-18)25(35)36)13-6-4-5-7-17(13)30-21)16(26(37)38-2)11-39-27(12)41-28-24(34)23(33)22(32)20(10-31)40-28/h3-7,11-12,14,18-20,22-24,27-34H,1,8-10H2,2H3,(H,35,36)/t12?,14?,18-,19?,20+,22+,23-,24+,27-,28-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(C2C=C)C[C@@H]2NC(Cc3c2[nH]c2c3cccc2)C(=O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502463
PubChem CID:	44575752
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
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
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]
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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	47100.0	nM	PMID[575372]

☑ 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 NPC475271 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	1277
0.2-0.3	4727
0.3-0.4	15843
0.4-0.5	14400
0.5-0.6	3710
0.6-0.7	2045
0.7-0.8	368
0.8-0.85	32
0.85-0.9	12
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC82070
0.9548	High Similarity	NPC476114
0.9406	High Similarity	NPC52254
0.905	High Similarity	NPC474905
0.8981	High Similarity	NPC174788
0.8972	High Similarity	NPC57453
0.8806	High Similarity	NPC476115
0.8564	High Similarity	NPC294909
0.8564	High Similarity	NPC254240
0.8564	High Similarity	NPC199851
0.8564	High Similarity	NPC312870
0.8564	High Similarity	NPC128265
0.8496	Intermediate Similarity	NPC473800
0.8302	Intermediate Similarity	NPC313640
0.825	Intermediate Similarity	NPC196251
0.825	Intermediate Similarity	NPC111602
0.825	Intermediate Similarity	NPC102338
0.825	Intermediate Similarity	NPC63199
0.8238	Intermediate Similarity	NPC477548
0.8119	Intermediate Similarity	NPC472112
0.8069	Intermediate Similarity	NPC175474
0.8039	Intermediate Similarity	NPC472113
0.803	Intermediate Similarity	NPC219336
0.8029	Intermediate Similarity	NPC81654
0.8029	Intermediate Similarity	NPC79129
0.8029	Intermediate Similarity	NPC313985
0.8029	Intermediate Similarity	NPC195461
0.8029	Intermediate Similarity	NPC249150
0.8029	Intermediate Similarity	NPC49196
0.8018	Intermediate Similarity	NPC281049
0.801	Intermediate Similarity	NPC245916
0.8	Intermediate Similarity	NPC234078
0.8	Intermediate Similarity	NPC221100
0.799	Intermediate Similarity	NPC469896
0.7981	Intermediate Similarity	NPC50997
0.7981	Intermediate Similarity	NPC160127
0.798	Intermediate Similarity	NPC217372
0.798	Intermediate Similarity	NPC15573
0.798	Intermediate Similarity	NPC183662
0.7964	Intermediate Similarity	NPC21638
0.7961	Intermediate Similarity	NPC220151
0.7961	Intermediate Similarity	NPC19692
0.7933	Intermediate Similarity	NPC52557
0.7933	Intermediate Similarity	NPC50503
0.789	Intermediate Similarity	NPC312645
0.7857	Intermediate Similarity	NPC33949
0.7854	Intermediate Similarity	NPC469501
0.7854	Intermediate Similarity	NPC469470
0.7848	Intermediate Similarity	NPC472762
0.7822	Intermediate Similarity	NPC472108
0.7822	Intermediate Similarity	NPC139291
0.7752	Intermediate Similarity	NPC89508
0.7752	Intermediate Similarity	NPC472291
0.7752	Intermediate Similarity	NPC229348
0.7729	Intermediate Similarity	NPC472097
0.7729	Intermediate Similarity	NPC127647
0.7703	Intermediate Similarity	NPC57994
0.7703	Intermediate Similarity	NPC289299
0.77	Intermediate Similarity	NPC476874
0.7696	Intermediate Similarity	NPC258480
0.7689	Intermediate Similarity	NPC214428
0.7675	Intermediate Similarity	NPC89987
0.7674	Intermediate Similarity	NPC238457
0.767	Intermediate Similarity	NPC472323
0.7647	Intermediate Similarity	NPC472110
0.7647	Intermediate Similarity	NPC472109
0.7639	Intermediate Similarity	NPC244741
0.7633	Intermediate Similarity	NPC182814
0.7621	Intermediate Similarity	NPC235684
0.7621	Intermediate Similarity	NPC66210
0.7615	Intermediate Similarity	NPC234999
0.7602	Intermediate Similarity	NPC148183
0.7602	Intermediate Similarity	NPC152768
0.76	Intermediate Similarity	NPC64216
0.7585	Intermediate Similarity	NPC328798
0.7581	Intermediate Similarity	NPC165599
0.7581	Intermediate Similarity	NPC476098
0.7569	Intermediate Similarity	NPC478158
0.7568	Intermediate Similarity	NPC249428
0.7561	Intermediate Similarity	NPC143533
0.7557	Intermediate Similarity	NPC478157
0.7557	Intermediate Similarity	NPC477979
0.7549	Intermediate Similarity	NPC15840
0.7545	Intermediate Similarity	NPC475778
0.7545	Intermediate Similarity	NPC111732
0.7545	Intermediate Similarity	NPC472099
0.7536	Intermediate Similarity	NPC20593
0.7524	Intermediate Similarity	NPC55493
0.7512	Intermediate Similarity	NPC277350
0.749	Intermediate Similarity	NPC191489
0.7489	Intermediate Similarity	NPC473105
0.7488	Intermediate Similarity	NPC318020
0.7488	Intermediate Similarity	NPC81802
0.7488	Intermediate Similarity	NPC472210
0.7488	Intermediate Similarity	NPC247735
0.7488	Intermediate Similarity	NPC472295
0.7488	Intermediate Similarity	NPC269886
0.7479	Intermediate Similarity	NPC476514
0.7477	Intermediate Similarity	NPC241024
0.7468	Intermediate Similarity	NPC184680
0.7449	Intermediate Similarity	NPC284685
0.7446	Intermediate Similarity	NPC474192
0.7446	Intermediate Similarity	NPC475720
0.7436	Intermediate Similarity	NPC470784
0.7436	Intermediate Similarity	NPC470785
0.7432	Intermediate Similarity	NPC54744
0.7431	Intermediate Similarity	NPC18661
0.7416	Intermediate Similarity	NPC325775
0.7415	Intermediate Similarity	NPC248041
0.7415	Intermediate Similarity	NPC283219
0.7415	Intermediate Similarity	NPC126709
0.7409	Intermediate Similarity	NPC469743
0.7404	Intermediate Similarity	NPC472107
0.7404	Intermediate Similarity	NPC79062
0.7402	Intermediate Similarity	NPC472122
0.7402	Intermediate Similarity	NPC24594
0.7391	Intermediate Similarity	NPC325093
0.7389	Intermediate Similarity	NPC472123
0.7387	Intermediate Similarity	NPC75634
0.7387	Intermediate Similarity	NPC118940
0.7383	Intermediate Similarity	NPC141454
0.7375	Intermediate Similarity	NPC476516
0.7373	Intermediate Similarity	NPC474116
0.7371	Intermediate Similarity	NPC54803
0.7371	Intermediate Similarity	NPC321592
0.7368	Intermediate Similarity	NPC315555
0.7368	Intermediate Similarity	NPC100734
0.7368	Intermediate Similarity	NPC315634
0.7368	Intermediate Similarity	NPC88923
0.7356	Intermediate Similarity	NPC472119
0.7349	Intermediate Similarity	NPC470499
0.7347	Intermediate Similarity	NPC472846
0.7346	Intermediate Similarity	NPC314333
0.7343	Intermediate Similarity	NPC113626
0.7343	Intermediate Similarity	NPC71037
0.7339	Intermediate Similarity	NPC315467
0.7336	Intermediate Similarity	NPC472293
0.7336	Intermediate Similarity	NPC472116
0.7331	Intermediate Similarity	NPC475816
0.733	Intermediate Similarity	NPC162860
0.7327	Intermediate Similarity	NPC317430
0.7321	Intermediate Similarity	NPC274842
0.7318	Intermediate Similarity	NPC156044
0.7317	Intermediate Similarity	NPC267885
0.7315	Intermediate Similarity	NPC472296
0.7315	Intermediate Similarity	NPC472297
0.7309	Intermediate Similarity	NPC207020
0.7309	Intermediate Similarity	NPC244856
0.7308	Intermediate Similarity	NPC472104
0.7308	Intermediate Similarity	NPC472444
0.7306	Intermediate Similarity	NPC478006
0.7306	Intermediate Similarity	NPC132539
0.7304	Intermediate Similarity	NPC24370
0.7304	Intermediate Similarity	NPC319232
0.7302	Intermediate Similarity	NPC469736
0.7301	Intermediate Similarity	NPC469594
0.7299	Intermediate Similarity	NPC46413
0.7295	Intermediate Similarity	NPC187827
0.7295	Intermediate Similarity	NPC472105
0.7295	Intermediate Similarity	NPC91179
0.7294	Intermediate Similarity	NPC162730
0.7286	Intermediate Similarity	NPC478077
0.7284	Intermediate Similarity	NPC322135
0.7284	Intermediate Similarity	NPC223409
0.7284	Intermediate Similarity	NPC95240
0.7282	Intermediate Similarity	NPC326575
0.7282	Intermediate Similarity	NPC145885
0.7282	Intermediate Similarity	NPC14113
0.7282	Intermediate Similarity	NPC84827
0.7281	Intermediate Similarity	NPC2395
0.7277	Intermediate Similarity	NPC236424
0.7277	Intermediate Similarity	NPC472292
0.7277	Intermediate Similarity	NPC306644
0.7269	Intermediate Similarity	NPC149708
0.7268	Intermediate Similarity	NPC149155
0.7268	Intermediate Similarity	NPC203468
0.7268	Intermediate Similarity	NPC110500
0.7265	Intermediate Similarity	NPC284888
0.7265	Intermediate Similarity	NPC323752
0.7264	Intermediate Similarity	NPC329858
0.7261	Intermediate Similarity	NPC235885
0.7254	Intermediate Similarity	NPC472435
0.7241	Intermediate Similarity	NPC100547
0.724	Intermediate Similarity	NPC478009
0.724	Intermediate Similarity	NPC478010
0.724	Intermediate Similarity	NPC54420
0.724	Intermediate Similarity	NPC323927
0.7236	Intermediate Similarity	NPC472436
0.7231	Intermediate Similarity	NPC165964
0.723	Intermediate Similarity	NPC243716
0.7229	Intermediate Similarity	NPC79107
0.7229	Intermediate Similarity	NPC475424
0.7227	Intermediate Similarity	NPC12944
0.7227	Intermediate Similarity	NPC25442
0.7225	Intermediate Similarity	NPC327373
0.7225	Intermediate Similarity	NPC322043
0.7225	Intermediate Similarity	NPC469358
0.7225	Intermediate Similarity	NPC303658
0.7215	Intermediate Similarity	NPC193761
0.7215	Intermediate Similarity	NPC155143

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 NPC475271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	438
0.2-0.3	653
0.3-0.4	1697
0.4-0.5	3002
0.5-0.6	2473
0.6-0.7	652
0.7-0.8	63
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8564	High Similarity	NPD4500	Approved
0.8564	High Similarity	NPD4501	Approved
0.8029	Intermediate Similarity	NPD4601	Approved
0.8029	Intermediate Similarity	NPD4600	Approved
0.7727	Intermediate Similarity	NPD8326	Phase 3
0.7727	Intermediate Similarity	NPD8325	Phase 3
0.7727	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4602	Approved
0.7632	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5003	Discontinued
0.749	Intermediate Similarity	NPD7708	Approved
0.7476	Intermediate Similarity	NPD2092	Phase 2
0.7476	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD2095	Phase 2
0.7476	Intermediate Similarity	NPD2094	Phase 2
0.7455	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7956	Approved
0.7449	Intermediate Similarity	NPD7955	Approved
0.7446	Intermediate Similarity	NPD4885	Approved
0.744	Intermediate Similarity	NPD2091	Phase 2
0.744	Intermediate Similarity	NPD2096	Phase 2
0.7431	Intermediate Similarity	NPD7957	Phase 1
0.7431	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7470	Discontinued
0.7409	Intermediate Similarity	NPD4506	Discontinued
0.7395	Intermediate Similarity	NPD6249	Phase 2
0.7395	Intermediate Similarity	NPD6248	Phase 2
0.7387	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7803	Approved
0.7364	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4499	Approved
0.7345	Intermediate Similarity	NPD6770	Approved
0.7327	Intermediate Similarity	NPD7727	Phase 2
0.7306	Intermediate Similarity	NPD8115	Approved
0.7306	Intermediate Similarity	NPD8114	Approved
0.7289	Intermediate Similarity	NPD3394	Approved
0.7289	Intermediate Similarity	NPD3393	Approved
0.7289	Intermediate Similarity	NPD3389	Approved
0.7273	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD482	Approved
0.7264	Intermediate Similarity	NPD2565	Phase 2
0.7264	Intermediate Similarity	NPD2564	Approved
0.7252	Intermediate Similarity	NPD4520	Approved
0.7244	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8399	Phase 1
0.7207	Intermediate Similarity	NPD8423	Phase 2
0.7195	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5487	Phase 1
0.7182	Intermediate Similarity	NPD8072	Approved
0.716	Intermediate Similarity	NPD5482	Discontinued
0.7156	Intermediate Similarity	NPD5075	Discontinued
0.715	Intermediate Similarity	NPD5104	Approved
0.7143	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7731	Approved
0.7124	Intermediate Similarity	NPD7730	Approved
0.7119	Intermediate Similarity	NPD7951	Approved
0.7119	Intermediate Similarity	NPD7789	Approved
0.7119	Intermediate Similarity	NPD7790	Approved
0.7119	Intermediate Similarity	NPD7952	Approved
0.7119	Intermediate Similarity	NPD7791	Approved
0.7119	Intermediate Similarity	NPD7950	Approved
0.7119	Intermediate Similarity	NPD7953	Approved
0.7112	Intermediate Similarity	NPD7271	Approved
0.7107	Intermediate Similarity	NPD8468	Phase 2
0.71	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7817	Phase 1
0.7078	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5632	Approved
0.7073	Intermediate Similarity	NPD2844	Phase 3
0.7072	Intermediate Similarity	NPD5901	Discontinued
0.707	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7824	Approved
0.7059	Intermediate Similarity	NPD8073	Approved
0.7059	Intermediate Similarity	NPD2915	Discontinued
0.7056	Intermediate Similarity	NPD4334	Discontinued
0.7054	Intermediate Similarity	NPD2510	Approved
0.7054	Intermediate Similarity	NPD2509	Approved
0.7053	Intermediate Similarity	NPD750	Phase 2
0.7042	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3003	Approved
0.7032	Intermediate Similarity	NPD7777	Approved
0.7032	Intermediate Similarity	NPD53	Approved
0.7032	Intermediate Similarity	NPD7778	Approved
0.7027	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7781	Approved
0.7021	Intermediate Similarity	NPD7780	Approved
0.7014	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8289	Discontinued
0.7005	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8272	Phase 2
0.6992	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6206	Phase 1
0.6977	Remote Similarity	NPD8466	Approved
0.6977	Remote Similarity	NPD8465	Approved
0.6977	Remote Similarity	NPD8467	Approved
0.6972	Remote Similarity	NPD7944	Discontinued
0.6967	Remote Similarity	NPD5897	Approved
0.6967	Remote Similarity	NPD5899	Approved
0.6967	Remote Similarity	NPD5898	Approved
0.6957	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6261	Phase 3
0.6953	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2920	Discontinued
0.6951	Remote Similarity	NPD6176	Phase 1
0.6941	Remote Similarity	NPD8364	Approved
0.6941	Remote Similarity	NPD8363	Approved
0.6926	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1768	Approved
0.6923	Remote Similarity	NPD7716	Approved
0.6923	Remote Similarity	NPD7717	Approved
0.692	Remote Similarity	NPD8282	Approved
0.692	Remote Similarity	NPD8374	Phase 3
0.692	Remote Similarity	NPD8283	Approved
0.692	Remote Similarity	NPD56	Approved
0.6904	Remote Similarity	NPD7558	Phase 2
0.69	Remote Similarity	NPD3795	Approved
0.69	Remote Similarity	NPD3794	Approved
0.6898	Remote Similarity	NPD7234	Approved
0.6898	Remote Similarity	NPD7233	Approved
0.6897	Remote Similarity	NPD7194	Discontinued
0.6892	Remote Similarity	NPD484	Approved
0.6892	Remote Similarity	NPD6479	Discontinued
0.689	Remote Similarity	NPD5450	Discontinued
0.6887	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5444	Phase 1
0.6881	Remote Similarity	NPD4315	Phase 2
0.688	Remote Similarity	NPD8255	Phase 2
0.6875	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8329	Phase 3
0.6872	Remote Similarity	NPD6641	Approved
0.6872	Remote Similarity	NPD6642	Approved
0.6872	Remote Similarity	NPD6529	Discontinued
0.687	Remote Similarity	NPD8425	Approved
0.687	Remote Similarity	NPD8459	Approved
0.687	Remote Similarity	NPD8426	Approved
0.687	Remote Similarity	NPD8460	Approved
0.687	Remote Similarity	NPD5903	Approved
0.687	Remote Similarity	NPD4897	Phase 2
0.687	Remote Similarity	NPD5902	Approved
0.6867	Remote Similarity	NPD8463	Approved
0.6858	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7878	Phase 2
0.6846	Remote Similarity	NPD8429	Approved
0.6846	Remote Similarity	NPD8428	Approved
0.6846	Remote Similarity	NPD8427	Approved
0.6844	Remote Similarity	NPD8098	Approved
0.6842	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7688	Phase 1
0.6812	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.681	Remote Similarity	NPD43	Approved
0.681	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6182	Approved
0.6804	Remote Similarity	NPD6665	Discontinued
0.6802	Remote Similarity	NPD7946	Pre-registration
0.6802	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4397	Phase 1
0.68	Remote Similarity	NPD8370	Discontinued
0.6798	Remote Similarity	NPD5834	Phase 3
0.6798	Remote Similarity	NPD5835	Phase 3
0.6793	Remote Similarity	NPD7603	Discontinued
0.6792	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7483	Phase 2
0.6791	Remote Similarity	NPD7482	Phase 2
0.6784	Remote Similarity	NPD8322	Phase 2
0.6783	Remote Similarity	NPD7573	Discontinued
0.6777	Remote Similarity	NPD3006	Discontinued
0.6777	Remote Similarity	NPD8421	Discontinued
0.6776	Remote Similarity	NPD6716	Phase 1
0.677	Remote Similarity	NPD5426	Phase 3
0.6765	Remote Similarity	NPD4086	Phase 1
0.6761	Remote Similarity	NPD8375	Approved
0.6758	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5913	Phase 3
0.6753	Remote Similarity	NPD3243	Approved
0.6745	Remote Similarity	NPD2382	Approved
0.6745	Remote Similarity	NPD2381	Approved
0.6745	Remote Similarity	NPD2380	Approved
0.6744	Remote Similarity	NPD5596	Phase 2
0.6742	Remote Similarity	NPD7619	Phase 3
0.6742	Remote Similarity	NPD4427	Phase 2
0.6742	Remote Similarity	NPD7618	Phase 3
0.674	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7970	Approved
0.6724	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7797	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