NPASS Compound

Structure

NPC473800 OpenBabel07101719252D 42 46 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 9.0023 -3.0181 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 7.4200 -3.7226 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 8.4145 -3.8271 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 4.3301 0.5000 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 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 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 -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 8.8212 -4.7406 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 39 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 19 1 0 0 0 0 9 31 1 0 0 0 0 10 16 2 0 0 0 0 10 40 1 0 0 0 0 11 32 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 9 1 6 0 0 0 20 22 1 0 0 0 0 20 41 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 28 1 0 0 0 0 24 35 1 1 0 0 0 25 36 1 0 0 0 0 25 37 2 0 0 0 0 26 38 2 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 27 42 1 6 0 0 0 28 41 1 0 0 0 0 28 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.18
Volume:	551.173
LogP:	0.745
LogD:	-0.111
LogS:	-2.684
# Rotatable Bonds:	8
TPSA:	221.12
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	5.105
Fsp3:	0.393
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:	-6.302
MDCK Permeability:	5.078920821688371e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.82
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	85.81245422363281%
Volume Distribution (VD):	0.434
Pgp-substrate:	18.97087287902832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	1.288
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.038
Carcinogencity:	0.368
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC473800

Natural Product ID:	NPC473800
*Common Name:**	Cordifoline
IUPAC Name:	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]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:	Cordifoline
Standard InCHIKey:	HFPKTEZZZRPDQU-XNKVVINBSA-N
Standard InCHI:	InChI=1S/C28H30N2O12/c1-3-12-13(7-18-21-15(8-19(29-18)25(36)37)14-6-11(32)4-5-17(14)30-21)16(26(38)39-2)10-40-27(12)42-28-24(35)23(34)22(33)20(9-31)41-28/h3-6,8,10,12-13,20,22-24,27-28,30-35H,1,7,9H2,2H3,(H,36,37)/t12?,13?,20-,22-,23+,24-,27+,28+/m1/s1
SMILES:	C=CC1[C@@H](OC=C(C1Cc1nc(cc2c1[nH]c1c2cc(cc1)O)C(=O)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452188
PubChem CID:	44575749
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	=	18300.0	nM	PMID[486908]

☑ 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 NPC473800 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	396
0.1-0.2	1760
0.2-0.3	6030
0.3-0.4	11493
0.4-0.5	14075
0.5-0.6	6592
0.6-0.7	2042
0.7-0.8	284
0.8-0.85	21
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9455	High Similarity	NPC57453
0.8496	Intermediate Similarity	NPC475271
0.8475	Intermediate Similarity	NPC312645
0.8341	Intermediate Similarity	NPC89508
0.8274	Intermediate Similarity	NPC82070
0.8235	Intermediate Similarity	NPC244741
0.8186	Intermediate Similarity	NPC476114
0.814	Intermediate Similarity	NPC165964
0.81	Intermediate Similarity	NPC165599
0.8079	Intermediate Similarity	NPC52254
0.7991	Intermediate Similarity	NPC321428
0.7911	Intermediate Similarity	NPC474905
0.7909	Intermediate Similarity	NPC141454
0.7857	Intermediate Similarity	NPC476115
0.7802	Intermediate Similarity	NPC174788
0.7787	Intermediate Similarity	NPC291609
0.7778	Intermediate Similarity	NPC476098
0.7778	Intermediate Similarity	NPC215837
0.7778	Intermediate Similarity	NPC475844
0.7746	Intermediate Similarity	NPC124300
0.7743	Intermediate Similarity	NPC132539
0.7741	Intermediate Similarity	NPC474701
0.7738	Intermediate Similarity	NPC191489
0.7727	Intermediate Similarity	NPC15801
0.7724	Intermediate Similarity	NPC310618
0.7718	Intermediate Similarity	NPC182222
0.7704	Intermediate Similarity	NPC473639
0.7679	Intermediate Similarity	NPC21638
0.7675	Intermediate Similarity	NPC270918
0.7672	Intermediate Similarity	NPC477979
0.7672	Intermediate Similarity	NPC118228
0.7663	Intermediate Similarity	NPC172355
0.7662	Intermediate Similarity	NPC244856
0.766	Intermediate Similarity	NPC472099
0.7659	Intermediate Similarity	NPC258048
0.7649	Intermediate Similarity	NPC472435
0.7635	Intermediate Similarity	NPC474192
0.7635	Intermediate Similarity	NPC475720
0.7617	Intermediate Similarity	NPC315634
0.7617	Intermediate Similarity	NPC88923
0.7617	Intermediate Similarity	NPC100734
0.7613	Intermediate Similarity	NPC477549
0.7609	Intermediate Similarity	NPC325297
0.76	Intermediate Similarity	NPC280714
0.7588	Intermediate Similarity	NPC227824
0.7586	Intermediate Similarity	NPC118940
0.7574	Intermediate Similarity	NPC184408
0.7563	Intermediate Similarity	NPC51388
0.7561	Intermediate Similarity	NPC148889
0.7559	Intermediate Similarity	NPC472436
0.7555	Intermediate Similarity	NPC300156
0.7554	Intermediate Similarity	NPC306644
0.7554	Intermediate Similarity	NPC236424
0.7544	Intermediate Similarity	NPC223427
0.7521	Intermediate Similarity	NPC274842
0.7521	Intermediate Similarity	NPC474688
0.752	Intermediate Similarity	NPC475816
0.751	Intermediate Similarity	NPC152620
0.749	Intermediate Similarity	NPC207686
0.749	Intermediate Similarity	NPC284685
0.7479	Intermediate Similarity	NPC280799
0.7468	Intermediate Similarity	NPC9894
0.7468	Intermediate Similarity	NPC294375
0.746	Intermediate Similarity	NPC67401
0.7457	Intermediate Similarity	NPC477548
0.7438	Intermediate Similarity	NPC274640
0.7425	Intermediate Similarity	NPC5145
0.7422	Intermediate Similarity	NPC276517
0.7419	Intermediate Similarity	NPC49672
0.7419	Intermediate Similarity	NPC99891
0.7415	Intermediate Similarity	NPC322064
0.7415	Intermediate Similarity	NPC148183
0.7415	Intermediate Similarity	NPC152768
0.7415	Intermediate Similarity	NPC469928
0.7414	Intermediate Similarity	NPC39679
0.7412	Intermediate Similarity	NPC294909
0.7412	Intermediate Similarity	NPC199851
0.7412	Intermediate Similarity	NPC254240
0.7412	Intermediate Similarity	NPC312870
0.7412	Intermediate Similarity	NPC53534
0.7412	Intermediate Similarity	NPC128265
0.7404	Intermediate Similarity	NPC234078
0.7404	Intermediate Similarity	NPC221100
0.7404	Intermediate Similarity	NPC39500
0.7403	Intermediate Similarity	NPC45190
0.7403	Intermediate Similarity	NPC475841
0.7403	Intermediate Similarity	NPC474145
0.74	Intermediate Similarity	NPC472434
0.7397	Intermediate Similarity	NPC478078
0.7395	Intermediate Similarity	NPC74360
0.7393	Intermediate Similarity	NPC89549
0.7385	Intermediate Similarity	NPC315467
0.7378	Intermediate Similarity	NPC314222
0.7378	Intermediate Similarity	NPC196449
0.7377	Intermediate Similarity	NPC260434
0.7371	Intermediate Similarity	NPC53344
0.7366	Intermediate Similarity	NPC33949
0.7354	Intermediate Similarity	NPC478006
0.7354	Intermediate Similarity	NPC74619
0.735	Intermediate Similarity	NPC314834
0.7341	Intermediate Similarity	NPC218388
0.7339	Intermediate Similarity	NPC470784
0.7336	Intermediate Similarity	NPC249040
0.7323	Intermediate Similarity	NPC181081
0.7319	Intermediate Similarity	NPC87413
0.7317	Intermediate Similarity	NPC473105
0.7311	Intermediate Similarity	NPC249428
0.7303	Intermediate Similarity	NPC144452
0.7298	Intermediate Similarity	NPC184680
0.7296	Intermediate Similarity	NPC88008
0.7296	Intermediate Similarity	NPC283117
0.7296	Intermediate Similarity	NPC314297
0.7296	Intermediate Similarity	NPC315545
0.7295	Intermediate Similarity	NPC194740
0.7292	Intermediate Similarity	NPC323969
0.729	Intermediate Similarity	NPC478010
0.729	Intermediate Similarity	NPC478009
0.7287	Intermediate Similarity	NPC129897
0.7284	Intermediate Similarity	NPC314648
0.7276	Intermediate Similarity	NPC321592
0.7276	Intermediate Similarity	NPC54803
0.7273	Intermediate Similarity	NPC229893
0.7273	Intermediate Similarity	NPC107836
0.7269	Intermediate Similarity	NPC470785
0.7269	Intermediate Similarity	NPC3207
0.7261	Intermediate Similarity	NPC60621
0.7257	Intermediate Similarity	NPC151781
0.7257	Intermediate Similarity	NPC316181
0.7257	Intermediate Similarity	NPC74562
0.7254	Intermediate Similarity	NPC157931
0.7253	Intermediate Similarity	NPC313345
0.7253	Intermediate Similarity	NPC313796
0.7253	Intermediate Similarity	NPC315638
0.7253	Intermediate Similarity	NPC314855
0.7253	Intermediate Similarity	NPC472286
0.7253	Intermediate Similarity	NPC472287
0.7251	Intermediate Similarity	NPC470901
0.7243	Intermediate Similarity	NPC179287
0.724	Intermediate Similarity	NPC314394
0.7238	Intermediate Similarity	NPC27041
0.7238	Intermediate Similarity	NPC472285
0.7238	Intermediate Similarity	NPC293151
0.7237	Intermediate Similarity	NPC303374
0.7233	Intermediate Similarity	NPC178858
0.7229	Intermediate Similarity	NPC6786
0.7225	Intermediate Similarity	NPC230403
0.7224	Intermediate Similarity	NPC311906
0.7222	Intermediate Similarity	NPC188400
0.722	Intermediate Similarity	NPC174760
0.7215	Intermediate Similarity	NPC472098
0.7208	Intermediate Similarity	NPC96321
0.7208	Intermediate Similarity	NPC469594
0.7203	Intermediate Similarity	NPC123839
0.72	Intermediate Similarity	NPC82472
0.7198	Intermediate Similarity	NPC329982
0.7198	Intermediate Similarity	NPC57398
0.7195	Intermediate Similarity	NPC322135
0.7195	Intermediate Similarity	NPC223409
0.7195	Intermediate Similarity	NPC95240
0.7189	Intermediate Similarity	NPC272549
0.7188	Intermediate Similarity	NPC194040
0.7185	Intermediate Similarity	NPC472291
0.7183	Intermediate Similarity	NPC295452
0.7183	Intermediate Similarity	NPC171393
0.7179	Intermediate Similarity	NPC472111
0.7178	Intermediate Similarity	NPC288987
0.7177	Intermediate Similarity	NPC284888
0.7174	Intermediate Similarity	NPC306376
0.7173	Intermediate Similarity	NPC187501
0.7167	Intermediate Similarity	NPC317572
0.7167	Intermediate Similarity	NPC115282
0.7154	Intermediate Similarity	NPC478011
0.7154	Intermediate Similarity	NPC478012
0.7154	Intermediate Similarity	NPC100547
0.7149	Intermediate Similarity	NPC276657
0.7149	Intermediate Similarity	NPC4687
0.7149	Intermediate Similarity	NPC39370
0.7149	Intermediate Similarity	NPC150239
0.7149	Intermediate Similarity	NPC97902
0.7148	Intermediate Similarity	NPC314056
0.7143	Intermediate Similarity	NPC24370
0.7143	Intermediate Similarity	NPC319232
0.7143	Intermediate Similarity	NPC111732
0.7143	Intermediate Similarity	NPC472589
0.7137	Intermediate Similarity	NPC473186
0.7132	Intermediate Similarity	NPC314882
0.7131	Intermediate Similarity	NPC122436
0.7127	Intermediate Similarity	NPC314176
0.7125	Intermediate Similarity	NPC74969
0.7124	Intermediate Similarity	NPC196251
0.7124	Intermediate Similarity	NPC63199
0.7124	Intermediate Similarity	NPC111602
0.7124	Intermediate Similarity	NPC102338
0.7119	Intermediate Similarity	NPC266249
0.7114	Intermediate Similarity	NPC124920
0.7114	Intermediate Similarity	NPC118559
0.7114	Intermediate Similarity	NPC261251
0.7114	Intermediate Similarity	NPC304307
0.7114	Intermediate Similarity	NPC34580
0.7113	Intermediate Similarity	NPC469592

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 NPC473800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	553
0.2-0.3	836
0.3-0.4	1842
0.4-0.5	2989
0.5-0.6	2025
0.6-0.7	598
0.7-0.8	52
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
0.805	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD5482	Discontinued
0.7738	Intermediate Similarity	NPD7708	Approved
0.7737	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7803	Approved
0.7549	Intermediate Similarity	NPD5450	Discontinued
0.7521	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD7955	Approved
0.749	Intermediate Similarity	NPD4885	Approved
0.749	Intermediate Similarity	NPD7956	Approved
0.7442	Intermediate Similarity	NPD6456	Discontinued
0.7412	Intermediate Similarity	NPD4501	Approved
0.7412	Intermediate Similarity	NPD4500	Approved
0.7393	Intermediate Similarity	NPD5416	Discontinued
0.7357	Intermediate Similarity	NPD5003	Discontinued
0.7333	Intermediate Similarity	NPD8463	Approved
0.7308	Intermediate Similarity	NPD4506	Discontinued
0.73	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4897	Phase 2
0.728	Intermediate Similarity	NPD5632	Approved
0.7205	Intermediate Similarity	NPD3328	Phase 2
0.7197	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4328	Approved
0.7176	Intermediate Similarity	NPD4558	Phase 2
0.7175	Intermediate Similarity	NPD7181	Phase 3
0.7126	Intermediate Similarity	NPD6531	Approved
0.7126	Intermediate Similarity	NPD6530	Approved
0.7119	Intermediate Similarity	NPD5507	Approved
0.7119	Intermediate Similarity	NPD5506	Approved
0.7115	Intermediate Similarity	NPD6716	Phase 1
0.7112	Intermediate Similarity	NPD484	Approved
0.7107	Intermediate Similarity	NPD6770	Approved
0.7107	Intermediate Similarity	NPD3258	Approved
0.7098	Intermediate Similarity	NPD5488	Discontinued
0.7092	Intermediate Similarity	NPD5805	Approved
0.708	Intermediate Similarity	NPD2951	Discontinued
0.7078	Intermediate Similarity	NPD6242	Discontinued
0.7073	Intermediate Similarity	NPD3263	Phase 3
0.7071	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8363	Approved
0.7068	Intermediate Similarity	NPD8364	Approved
0.7066	Intermediate Similarity	NPD7395	Discontinued
0.7066	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8370	Discontinued
0.7052	Intermediate Similarity	NPD3006	Discontinued
0.7046	Intermediate Similarity	NPD6376	Discontinued
0.704	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4601	Approved
0.7039	Intermediate Similarity	NPD4600	Approved
0.7037	Intermediate Similarity	NPD8466	Approved
0.7037	Intermediate Similarity	NPD8467	Approved
0.7037	Intermediate Similarity	NPD8465	Approved
0.7021	Intermediate Similarity	NPD8421	Discontinued
0.702	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2565	Phase 2
0.7018	Intermediate Similarity	NPD2564	Approved
0.7015	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5512	Phase 3
0.7012	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3746	Discontinued
0.6988	Remote Similarity	NPD5022	Discontinued
0.6988	Remote Similarity	NPD5479	Discontinued
0.6987	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5612	Discontinued
0.6972	Remote Similarity	NPD4373	Phase 2
0.6971	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD5164	Discontinued
0.6942	Remote Similarity	NPD3257	Approved
0.6941	Remote Similarity	NPD7417	Discontinued
0.6935	Remote Similarity	NPD7603	Discontinued
0.6934	Remote Similarity	NPD8459	Approved
0.6934	Remote Similarity	NPD8426	Approved
0.6934	Remote Similarity	NPD8460	Approved
0.6934	Remote Similarity	NPD8425	Approved
0.6933	Remote Similarity	NPD5429	Discontinued
0.6932	Remote Similarity	NPD7797	Approved
0.6932	Remote Similarity	NPD7796	Approved
0.6923	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7853	Phase 2
0.6914	Remote Similarity	NPD3394	Approved
0.6914	Remote Similarity	NPD3393	Approved
0.6914	Remote Similarity	NPD3389	Approved
0.6912	Remote Similarity	NPD8429	Approved
0.6912	Remote Similarity	NPD8428	Approved
0.6912	Remote Similarity	NPD8427	Approved
0.6908	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7558	Phase 2
0.6904	Remote Similarity	NPD5658	Approved
0.6901	Remote Similarity	NPD3243	Approved
0.6892	Remote Similarity	NPD6962	Phase 2
0.6891	Remote Similarity	NPD3003	Approved
0.689	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD8358	Approved
0.6867	Remote Similarity	NPD6550	Discontinued
0.6862	Remote Similarity	NPD7222	Phase 2
0.6853	Remote Similarity	NPD4952	Phase 3
0.6849	Remote Similarity	NPD5901	Discontinued
0.6848	Remote Similarity	NPD6517	Phase 3
0.6846	Remote Similarity	NPD8102	Discontinued
0.6836	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD8468	Phase 2
0.6829	Remote Similarity	NPD7194	Discontinued
0.6829	Remote Similarity	NPD6974	Phase 3
0.6827	Remote Similarity	NPD3925	Approved
0.6825	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4368	Phase 2
0.682	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.682	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4502	Phase 2
0.6815	Remote Similarity	NPD6209	Approved
0.6808	Remote Similarity	NPD6276	Discontinued
0.6803	Remote Similarity	NPD5903	Approved
0.6803	Remote Similarity	NPD5902	Approved
0.68	Remote Similarity	NPD8289	Discontinued
0.6798	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5866	Approved
0.6789	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4038	Approved
0.6778	Remote Similarity	NPD4033	Approved
0.6778	Remote Similarity	NPD4035	Approved
0.6778	Remote Similarity	NPD4036	Approved
0.6778	Remote Similarity	NPD4122	Approved
0.6778	Remote Similarity	NPD31	Approved
0.6778	Remote Similarity	NPD4039	Approved
0.6778	Remote Similarity	NPD4037	Approved
0.6778	Remote Similarity	NPD32	Approved
0.6778	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4034	Approved
0.6773	Remote Similarity	NPD4086	Phase 1
0.6773	Remote Similarity	NPD7994	Phase 2
0.6773	Remote Similarity	NPD4845	Discontinued
0.6772	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8399	Phase 1
0.6763	Remote Similarity	NPD8423	Phase 2
0.676	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4602	Approved
0.6748	Remote Similarity	NPD8325	Phase 3
0.6748	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8326	Phase 3
0.6747	Remote Similarity	NPD8356	Approved
0.6745	Remote Similarity	NPD3074	Discontinued
0.6736	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2920	Discontinued
0.6732	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6290	Phase 2
0.6721	Remote Similarity	NPD4429	Discontinued
0.6717	Remote Similarity	NPD8442	Discontinued
0.6709	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2177	Approved
0.6709	Remote Similarity	NPD2176	Approved
0.6709	Remote Similarity	NPD1768	Approved
0.6709	Remote Similarity	NPD2175	Phase 3
0.6708	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8430	Approved
0.6694	Remote Similarity	NPD2510	Approved
0.6694	Remote Similarity	NPD3795	Approved
0.6694	Remote Similarity	NPD2916	Discontinued
0.6694	Remote Similarity	NPD3794	Approved
0.6694	Remote Similarity	NPD2509	Approved
0.6693	Remote Similarity	NPD1867	Approved
0.6692	Remote Similarity	NPD8101	Phase 3
0.6692	Remote Similarity	NPD3986	Discontinued
0.6692	Remote Similarity	NPD8255	Phase 2
0.6689	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2844	Phase 3
0.668	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4989	Phase 2
0.668	Remote Similarity	NPD7470	Discontinued
0.6679	Remote Similarity	NPD6228	Discontinued
0.6667	Remote Similarity	NPD7426	Phase 1
0.6667	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD8489	Phase 1
0.6667	Remote Similarity	NPD7946	Pre-registration
0.6653	Remote Similarity	NPD7878	Phase 2
0.6653	Remote Similarity	NPD7727	Phase 2
0.6653	Remote Similarity	NPD7452	Approved
0.6653	Remote Similarity	NPD7453	Approved
0.6641	Remote Similarity	NPD7886	Phase 2
0.6641	Remote Similarity	NPD7885	Phase 2
0.664	Remote Similarity	NPD3259	Approved
0.664	Remote Similarity	NPD8160	Phase 2
0.6639	Remote Similarity	NPD8115	Approved
0.6639	Remote Similarity	NPD8114	Approved
0.6638	Remote Similarity	NPD1038	Approved
0.6626	Remote Similarity	NPD3945	Discontinued
0.6625	Remote Similarity	NPD2779	Approved
0.6618	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5939	Approved
0.6612	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5936	Approved
0.661	Remote Similarity	NPD4418	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