NPASS Compound

Structure

CID277350 OpenBabel06191716082D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.2876 0.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1752 -2.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 -4.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4393 -0.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6471 -2.1599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8538 -0.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8538 -1.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 -0.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 -2.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7736 -2.3629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7419 -2.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2520 -0.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6540 -0.6349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8640 -0.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 -0.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 -1.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2454 -1.5497 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6820 -1.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3265 -3.2986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1506 -1.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6857 -0.6857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7123 -1.3980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2520 -2.1825 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1822 -1.4482 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5930 -3.6067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5908 -0.5334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0530 -3.9408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6787 -2.2107 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 4 2 0 0 0 0 2 5 1 0 0 0 0 3 27 1 0 0 0 0 5 28 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 4 1 6 0 0 0 21 29 1 0 0 0 0 22 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.18
Volume:	402.332
LogP:	3.161
LogD:	3.131
LogS:	-4.151
# Rotatable Bonds:	7
TPSA:	80.86
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	4.271
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115
MDCK Permeability:	2.547440817579627e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.566
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.853
Plasma Protein Binding (PPB):	83.39766693115234%
Volume Distribution (VD):	0.781
Pgp-substrate:	14.076847076416016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.34
CYP2C9-substrate:	0.464
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.462
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	4.801
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.769
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.154
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.059
Carcinogencity:	0.444
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.646

Download Data

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

Natural Product: NPC277350

Natural Product ID:	NPC277350
*Common Name:**	Alstolobine A
IUPAC Name:	6-O-ethyl 3-O-methyl (3S,3aR,7aS)-7a-ethenyl-3-(1H-indol-2-yl)-3a,4,5,7-tetrahydro-2H-furo[2,3-c]pyridine-3,6-dicarboxylate
Synonyms:	Alstolobine A
Standard InCHIKey:	XMPQHDBGVZIIJS-WTOYTKOKSA-N
Standard InCHI:	InChI=1S/C22H26N2O5/c1-4-21-13-24(20(26)28-5-2)11-10-17(21)22(14-29-21,19(25)27-3)18-12-15-8-6-7-9-16(15)23-18/h4,6-9,12,17,23H,1,5,10-11,13-14H2,2-3H3/t17-,21+,22-/m0/s1
SMILES:	CCOC(=O)N1CC[C@H]2[C@](C1)(C=C)OC[C@@]2(C(=O)OC)c1cc2c([nH]1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651110
PubChem CID:	50900050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[573223]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.51	ug.mL-1	PMID[573223]

☑ 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 NPC277350 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	304
0.1-0.2	1487
0.2-0.3	6610
0.3-0.4	22085
0.4-0.5	6791
0.5-0.6	2812
0.6-0.7	2080
0.7-0.8	509
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9617	High Similarity	NPC214428
0.9027	High Similarity	NPC55493
0.8646	High Similarity	NPC241024
0.8593	High Similarity	NPC475778
0.8586	High Similarity	NPC234999
0.8442	Intermediate Similarity	NPC469743
0.8438	Intermediate Similarity	NPC474121
0.8418	Intermediate Similarity	NPC162730
0.8325	Intermediate Similarity	NPC329858
0.8325	Intermediate Similarity	NPC474116
0.8325	Intermediate Similarity	NPC314333
0.8122	Intermediate Similarity	NPC52557
0.8098	Intermediate Similarity	NPC472291
0.8	Intermediate Similarity	NPC469896
0.799	Intermediate Similarity	NPC63199
0.799	Intermediate Similarity	NPC196251
0.799	Intermediate Similarity	NPC111602
0.799	Intermediate Similarity	NPC102338
0.799	Intermediate Similarity	NPC175474
0.7919	Intermediate Similarity	NPC472295
0.7919	Intermediate Similarity	NPC472210
0.7919	Intermediate Similarity	NPC269886
0.7919	Intermediate Similarity	NPC247735
0.7919	Intermediate Similarity	NPC81802
0.7902	Intermediate Similarity	NPC478158
0.7885	Intermediate Similarity	NPC478157
0.7885	Intermediate Similarity	NPC477979
0.7882	Intermediate Similarity	NPC185742
0.7882	Intermediate Similarity	NPC475847
0.7876	Intermediate Similarity	NPC472119
0.7837	Intermediate Similarity	NPC229348
0.7789	Intermediate Similarity	NPC19692
0.7789	Intermediate Similarity	NPC220151
0.7778	Intermediate Similarity	NPC311906
0.7773	Intermediate Similarity	NPC96321
0.7773	Intermediate Similarity	NPC281049
0.7772	Intermediate Similarity	NPC313985
0.7772	Intermediate Similarity	NPC199851
0.7772	Intermediate Similarity	NPC312870
0.7772	Intermediate Similarity	NPC49196
0.7772	Intermediate Similarity	NPC195461
0.7772	Intermediate Similarity	NPC79129
0.7772	Intermediate Similarity	NPC254240
0.7772	Intermediate Similarity	NPC294909
0.7772	Intermediate Similarity	NPC81654
0.7772	Intermediate Similarity	NPC249150
0.7772	Intermediate Similarity	NPC128265
0.7757	Intermediate Similarity	NPC64216
0.7751	Intermediate Similarity	NPC54744
0.775	Intermediate Similarity	NPC245916
0.7714	Intermediate Similarity	NPC474412
0.7689	Intermediate Similarity	NPC473041
0.7688	Intermediate Similarity	NPC472113
0.7678	Intermediate Similarity	NPC469928
0.7677	Intermediate Similarity	NPC472112
0.7673	Intermediate Similarity	NPC50503
0.7668	Intermediate Similarity	NPC219336
0.7642	Intermediate Similarity	NPC312645
0.7638	Intermediate Similarity	NPC472097
0.7635	Intermediate Similarity	NPC293917
0.7629	Intermediate Similarity	NPC91179
0.7617	Intermediate Similarity	NPC183662
0.7617	Intermediate Similarity	NPC145885
0.7617	Intermediate Similarity	NPC84827
0.7617	Intermediate Similarity	NPC217372
0.7617	Intermediate Similarity	NPC14113
0.7617	Intermediate Similarity	NPC15573
0.7614	Intermediate Similarity	NPC235684
0.761	Intermediate Similarity	NPC193761
0.761	Intermediate Similarity	NPC476874
0.7604	Intermediate Similarity	NPC472762
0.76	Intermediate Similarity	NPC472292
0.7594	Intermediate Similarity	NPC152768
0.7594	Intermediate Similarity	NPC330009
0.7594	Intermediate Similarity	NPC148183
0.7586	Intermediate Similarity	NPC67288
0.7578	Intermediate Similarity	NPC470785
0.7574	Intermediate Similarity	NPC472293
0.757	Intermediate Similarity	NPC52254
0.7549	Intermediate Similarity	NPC472296
0.7549	Intermediate Similarity	NPC472297
0.7545	Intermediate Similarity	NPC475816
0.7536	Intermediate Similarity	NPC118940
0.7536	Intermediate Similarity	NPC75634
0.7536	Intermediate Similarity	NPC132539
0.7534	Intermediate Similarity	NPC184680
0.7526	Intermediate Similarity	NPC14325
0.7526	Intermediate Similarity	NPC28848
0.7524	Intermediate Similarity	NPC137589
0.7524	Intermediate Similarity	NPC123839
0.7524	Intermediate Similarity	NPC155143
0.7512	Intermediate Similarity	NPC475271
0.7512	Intermediate Similarity	NPC36405
0.7511	Intermediate Similarity	NPC475720
0.7511	Intermediate Similarity	NPC474192
0.7511	Intermediate Similarity	NPC89987
0.75	Intermediate Similarity	NPC89508
0.75	Intermediate Similarity	NPC470784
0.75	Intermediate Similarity	NPC2395
0.7487	Intermediate Similarity	NPC472323
0.7478	Intermediate Similarity	NPC14812
0.7477	Intermediate Similarity	NPC235885
0.7477	Intermediate Similarity	NPC305984
0.7476	Intermediate Similarity	NPC475506
0.7475	Intermediate Similarity	NPC472107
0.7475	Intermediate Similarity	NPC79062
0.7466	Intermediate Similarity	NPC14288
0.7464	Intermediate Similarity	NPC477065
0.7462	Intermediate Similarity	NPC143533
0.7461	Intermediate Similarity	NPC161861
0.7455	Intermediate Similarity	NPC33949
0.7453	Intermediate Similarity	NPC472098
0.7452	Intermediate Similarity	NPC473376
0.7443	Intermediate Similarity	NPC24370
0.7443	Intermediate Similarity	NPC319232
0.7442	Intermediate Similarity	NPC82070
0.7442	Intermediate Similarity	NPC303658
0.7437	Intermediate Similarity	NPC160381
0.7437	Intermediate Similarity	NPC311858
0.7435	Intermediate Similarity	NPC470509
0.7429	Intermediate Similarity	NPC266249
0.7427	Intermediate Similarity	NPC471303
0.7421	Intermediate Similarity	NPC95240
0.7421	Intermediate Similarity	NPC322135
0.7415	Intermediate Similarity	NPC473640
0.7415	Intermediate Similarity	NPC149708
0.7409	Intermediate Similarity	NPC34580
0.7409	Intermediate Similarity	NPC475258
0.7409	Intermediate Similarity	NPC124920
0.7409	Intermediate Similarity	NPC118559
0.7409	Intermediate Similarity	NPC304307
0.7402	Intermediate Similarity	NPC79356
0.7402	Intermediate Similarity	NPC102592
0.7399	Intermediate Similarity	NPC473105
0.7398	Intermediate Similarity	NPC213468
0.7398	Intermediate Similarity	NPC283219
0.7398	Intermediate Similarity	NPC126709
0.7398	Intermediate Similarity	NPC248041
0.7393	Intermediate Similarity	NPC477548
0.7393	Intermediate Similarity	NPC162860
0.7387	Intermediate Similarity	NPC475859
0.7387	Intermediate Similarity	NPC474877
0.7387	Intermediate Similarity	NPC475969
0.7385	Intermediate Similarity	NPC84347
0.7385	Intermediate Similarity	NPC267885
0.7381	Intermediate Similarity	NPC54420
0.7381	Intermediate Similarity	NPC474905
0.7376	Intermediate Similarity	NPC138370
0.7376	Intermediate Similarity	NPC100547
0.7374	Intermediate Similarity	NPC19679
0.7374	Intermediate Similarity	NPC472108
0.7374	Intermediate Similarity	NPC139291
0.7373	Intermediate Similarity	NPC272174
0.7364	Intermediate Similarity	NPC475338
0.7364	Intermediate Similarity	NPC909
0.7363	Intermediate Similarity	NPC46413
0.7363	Intermediate Similarity	NPC213629
0.7363	Intermediate Similarity	NPC321708
0.7358	Intermediate Similarity	NPC471304
0.7356	Intermediate Similarity	NPC260900
0.7354	Intermediate Similarity	NPC54803
0.7354	Intermediate Similarity	NPC321592
0.7353	Intermediate Similarity	NPC57994
0.7353	Intermediate Similarity	NPC289299
0.735	Intermediate Similarity	NPC315555
0.7347	Intermediate Similarity	NPC111275
0.7347	Intermediate Similarity	NPC211997
0.7342	Intermediate Similarity	NPC470729
0.7342	Intermediate Similarity	NPC477175
0.7342	Intermediate Similarity	NPC477176
0.7342	Intermediate Similarity	NPC470730
0.7342	Intermediate Similarity	NPC223409
0.7339	Intermediate Similarity	NPC474896
0.7336	Intermediate Similarity	NPC221100
0.7336	Intermediate Similarity	NPC234078
0.7333	Intermediate Similarity	NPC203468
0.7333	Intermediate Similarity	NPC110500
0.7333	Intermediate Similarity	NPC149155
0.7333	Intermediate Similarity	NPC18661
0.733	Intermediate Similarity	NPC21174
0.733	Intermediate Similarity	NPC261251
0.733	Intermediate Similarity	NPC271797
0.7323	Intermediate Similarity	NPC71037
0.7321	Intermediate Similarity	NPC63279
0.7321	Intermediate Similarity	NPC323198
0.7321	Intermediate Similarity	NPC284888
0.7321	Intermediate Similarity	NPC165599
0.7321	Intermediate Similarity	NPC323752
0.7321	Intermediate Similarity	NPC476098
0.7318	Intermediate Similarity	NPC21638
0.7317	Intermediate Similarity	NPC472116
0.7317	Intermediate Similarity	NPC260909
0.7313	Intermediate Similarity	NPC17059
0.7311	Intermediate Similarity	NPC223791
0.7311	Intermediate Similarity	NPC107077
0.731	Intermediate Similarity	NPC472443
0.7309	Intermediate Similarity	NPC477177
0.7308	Intermediate Similarity	NPC300183
0.7306	Intermediate Similarity	NPC317430
0.7306	Intermediate Similarity	NPC31097

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 NPC277350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	501
0.2-0.3	645
0.3-0.4	1629
0.4-0.5	2687
0.5-0.6	2674
0.6-0.7	723
0.7-0.8	112
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8325	Intermediate Similarity	NPD4499	Approved
0.8256	Intermediate Similarity	NPD5003	Discontinued
0.81	Intermediate Similarity	NPD6176	Phase 1
0.8088	Intermediate Similarity	NPD7470	Discontinued
0.8041	Intermediate Similarity	NPD2564	Approved
0.8041	Intermediate Similarity	NPD2565	Phase 2
0.7921	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD2509	Approved
0.7854	Intermediate Similarity	NPD2510	Approved
0.7772	Intermediate Similarity	NPD4500	Approved
0.7772	Intermediate Similarity	NPD4600	Approved
0.7772	Intermediate Similarity	NPD4501	Approved
0.7772	Intermediate Similarity	NPD4601	Approved
0.7659	Intermediate Similarity	NPD2920	Discontinued
0.7653	Intermediate Similarity	NPD6770	Approved
0.7635	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD4334	Discontinued
0.7585	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD3389	Approved
0.7512	Intermediate Similarity	NPD3393	Approved
0.7512	Intermediate Similarity	NPD3394	Approved
0.75	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2844	Phase 3
0.7476	Intermediate Similarity	NPD4506	Discontinued
0.7465	Intermediate Similarity	NPD5293	Phase 2
0.7463	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6249	Phase 2
0.7463	Intermediate Similarity	NPD5913	Phase 3
0.7463	Intermediate Similarity	NPD6248	Phase 2
0.7462	Intermediate Similarity	NPD2094	Phase 2
0.7462	Intermediate Similarity	NPD2092	Phase 2
0.7462	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2095	Phase 2
0.7437	Intermediate Similarity	NPD5444	Phase 1
0.7426	Intermediate Similarity	NPD4315	Phase 2
0.7424	Intermediate Similarity	NPD2096	Phase 2
0.7424	Intermediate Similarity	NPD2091	Phase 2
0.7415	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7688	Phase 1
0.7385	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5596	Phase 2
0.7368	Intermediate Similarity	NPD5426	Phase 3
0.7353	Intermediate Similarity	NPD4602	Approved
0.7333	Intermediate Similarity	NPD482	Approved
0.7324	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5487	Phase 1
0.7317	Intermediate Similarity	NPD8459	Approved
0.7317	Intermediate Similarity	NPD8460	Approved
0.7309	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3947	Discontinued
0.7281	Intermediate Similarity	NPD5632	Approved
0.7277	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8399	Phase 1
0.7264	Intermediate Similarity	NPD8423	Phase 2
0.7261	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7001	Phase 3
0.7246	Intermediate Similarity	NPD7778	Approved
0.7246	Intermediate Similarity	NPD7777	Approved
0.7246	Intermediate Similarity	NPD53	Approved
0.7243	Intermediate Similarity	NPD5475	Discontinued
0.7238	Intermediate Similarity	NPD8072	Approved
0.7227	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD8466	Approved
0.7224	Intermediate Similarity	NPD8467	Approved
0.7224	Intermediate Similarity	NPD8465	Approved
0.7209	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8283	Approved
0.7204	Intermediate Similarity	NPD56	Approved
0.7204	Intermediate Similarity	NPD8282	Approved
0.7204	Intermediate Similarity	NPD8098	Approved
0.72	Intermediate Similarity	NPD4885	Approved
0.7198	Intermediate Similarity	NPD6206	Phase 1
0.7198	Intermediate Similarity	NPD8358	Approved
0.7196	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD750	Phase 2
0.719	Intermediate Similarity	NPD8363	Approved
0.719	Intermediate Similarity	NPD8073	Approved
0.719	Intermediate Similarity	NPD8364	Approved
0.7188	Intermediate Similarity	NPD7824	Approved
0.7165	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6261	Phase 3
0.7162	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8326	Phase 3
0.7156	Intermediate Similarity	NPD8325	Phase 3
0.7143	Intermediate Similarity	NPD4897	Phase 2
0.7143	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7970	Approved
0.7137	Intermediate Similarity	NPD5482	Discontinued
0.7131	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7878	Phase 2
0.7123	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5104	Approved
0.7109	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8425	Approved
0.7108	Intermediate Similarity	NPD8426	Approved
0.7105	Intermediate Similarity	NPD3006	Discontinued
0.7105	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4427	Phase 2
0.7098	Intermediate Similarity	NPD7730	Approved
0.7098	Intermediate Similarity	NPD7731	Approved
0.7093	Intermediate Similarity	NPD7950	Approved
0.7093	Intermediate Similarity	NPD7789	Approved
0.7093	Intermediate Similarity	NPD7791	Approved
0.7093	Intermediate Similarity	NPD7953	Approved
0.7093	Intermediate Similarity	NPD7951	Approved
0.7093	Intermediate Similarity	NPD7790	Approved
0.7093	Intermediate Similarity	NPD7952	Approved
0.7089	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7957	Phase 1
0.7085	Intermediate Similarity	NPD8429	Approved
0.7085	Intermediate Similarity	NPD8428	Approved
0.7085	Intermediate Similarity	NPD7271	Approved
0.7085	Intermediate Similarity	NPD8427	Approved
0.7083	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7946	Pre-registration
0.7072	Intermediate Similarity	NPD6995	Phase 1
0.7067	Intermediate Similarity	NPD7781	Approved
0.7067	Intermediate Similarity	NPD7780	Approved
0.7064	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4948	Discontinued
0.7056	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7573	Discontinued
0.7042	Intermediate Similarity	NPD5901	Discontinued
0.7042	Intermediate Similarity	NPD8272	Phase 2
0.704	Intermediate Similarity	NPD7716	Approved
0.704	Intermediate Similarity	NPD7717	Approved
0.7037	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD2915	Discontinued
0.7019	Intermediate Similarity	NPD7619	Phase 3
0.7019	Intermediate Similarity	NPD7618	Phase 3
0.7015	Intermediate Similarity	NPD5899	Approved
0.7015	Intermediate Similarity	NPD5897	Approved
0.7015	Intermediate Similarity	NPD5898	Approved
0.7014	Intermediate Similarity	NPD484	Approved
0.7014	Intermediate Similarity	NPD6479	Discontinued
0.7014	Intermediate Similarity	NPD5427	Suspended
0.7009	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7955	Approved
0.7	Intermediate Similarity	NPD7956	Approved
0.6995	Remote Similarity	NPD2214	Approved
0.6995	Remote Similarity	NPD2213	Approved
0.6991	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5512	Phase 3
0.6982	Remote Similarity	NPD1996	Discontinued
0.6981	Remote Similarity	NPD7727	Phase 2
0.6978	Remote Similarity	NPD7711	Discontinued
0.6977	Remote Similarity	NPD8322	Phase 2
0.6977	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8096	Phase 3
0.6972	Remote Similarity	NPD8097	Phase 3
0.6971	Remote Similarity	NPD7708	Approved
0.697	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6999	Discontinued
0.6963	Remote Similarity	NPD8114	Approved
0.6963	Remote Similarity	NPD8115	Approved
0.6961	Remote Similarity	NPD5075	Discontinued
0.696	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4952	Phase 3
0.6959	Remote Similarity	NPD2511	Approved
0.6959	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5891	Approved
0.6955	Remote Similarity	NPD8160	Phase 2
0.6951	Remote Similarity	NPD5506	Approved
0.6951	Remote Similarity	NPD5507	Approved
0.6942	Remote Similarity	NPD1534	Approved
0.6938	Remote Similarity	NPD7944	Discontinued
0.6927	Remote Similarity	NPD5256	Discontinued
0.6926	Remote Similarity	NPD7803	Approved
0.6923	Remote Similarity	NPD6665	Discontinued
0.6919	Remote Similarity	NPD4397	Phase 1
0.6915	Remote Similarity	NPD6642	Approved
0.6915	Remote Similarity	NPD6641	Approved
0.6915	Remote Similarity	NPD2144	Approved
0.6912	Remote Similarity	NPD4520	Approved
0.6905	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7603	Discontinued
0.6901	Remote Similarity	NPD7817	Phase 1
0.6897	Remote Similarity	NPD3038	Discontinued
0.6895	Remote Similarity	NPD7454	Approved
0.6895	Remote Similarity	NPD7455	Approved
0.6895	Remote Similarity	NPD8093	Discontinued
0.6883	Remote Similarity	NPD7853	Phase 2

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