NPASS Compound

Structure

NPC79062 OpenBabel07101719242D 25 29 0 0 1 0 0 0 0 0999 V2000 -5.3816 0.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2371 0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5943 -2.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -1.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 -2.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 -0.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 0.2262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6768 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 1.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 -1.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1209 -1.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1804 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8506 -1.3764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 0.1310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1804 -1.0253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6466 -0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 -1.5059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8263 0.0547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9253 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6525 -0.5087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7140 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -1.0253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 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 18 2 0 0 0 0 9 15 1 0 0 0 0 10 24 2 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 16 10 1 1 0 0 0 17 11 1 6 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 9 1 1 0 0 0 19 22 1 0 0 0 0 20 8 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.2
Volume:	355.382
LogP:	2.768
LogD:	2.97
LogS:	-3.297
# Rotatable Bonds:	1
TPSA:	34.47
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	5.164
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981
MDCK Permeability:	2.853197293006815e-05
Pgp-inhibitor:	0.859
Pgp-substrate:	0.575
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.098
30% Bioavailability (F30%):	0.236

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	61.92558288574219%
Volume Distribution (VD):	1.909
Pgp-substrate:	46.87993621826172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.574
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.657
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.866

ADMET: Excretion

Clearance (CL):	11.067
Half-life (T1/2):	0.259

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.347
Rat Oral Acute Toxicity:	0.381
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.734
Carcinogencity:	0.685
Eye Corrosion:	0.013
Eye Irritation:	0.047
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC79062

Natural Product ID:	NPC79062
*Common Name:**	Talcarpine
IUPAC Name:	n.a.
Synonyms:	Talcarpine
Standard InCHIKey:	NTXSRNQQLHZNTH-YONURWJNSA-N
Standard InCHI:	InChI=1S/C21H26N2O2/c1-12-16(10-24)14-8-20-21-15(9-19(22(20)2)17(14)11-25-12)13-6-4-5-7-18(13)23(21)3/h4-7,10,12,14,16-17,19-20H,8-9,11H2,1-3H3/t12-,14-,16+,17+,19-,20-/m0/s1
SMILES:	O=C[C@@H]1[C@H](C)OC[C@@H]2[C@H]1C[C@@H]1N([C@H]2Cc2c1n(C)c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332140
PubChem CID:	11131571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline alkaloids

*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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19678	Alstonia macrophylla	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
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[452841]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[452842]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[452842]

☑ 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 NPC79062 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	290
0.1-0.2	1471
0.2-0.3	7868
0.3-0.4	22995
0.4-0.5	5098
0.5-0.6	2446
0.6-0.7	2118
0.7-0.8	338
0.8-0.85	56
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472107
0.9467	High Similarity	NPC66210
0.9235	High Similarity	NPC258480
0.9172	High Similarity	NPC15840
0.9012	High Similarity	NPC472119
0.8977	High Similarity	NPC472113
0.8941	High Similarity	NPC234987
0.8857	High Similarity	NPC472323
0.8844	High Similarity	NPC143533
0.8827	High Similarity	NPC245916
0.8814	High Similarity	NPC472097
0.8772	High Similarity	NPC472122
0.8772	High Similarity	NPC24594
0.8757	High Similarity	NPC472112
0.8736	High Similarity	NPC472104
0.8678	High Similarity	NPC113626
0.8621	High Similarity	NPC472105
0.8621	High Similarity	NPC187827
0.8588	High Similarity	NPC478077
0.8525	High Similarity	NPC52557
0.8523	High Similarity	NPC472110
0.8523	High Similarity	NPC472109
0.8512	High Similarity	NPC81229
0.8512	High Similarity	NPC255229
0.8492	Intermediate Similarity	NPC175474
0.8432	Intermediate Similarity	NPC81654
0.8432	Intermediate Similarity	NPC195461
0.8432	Intermediate Similarity	NPC313985
0.8432	Intermediate Similarity	NPC249150
0.8432	Intermediate Similarity	NPC79129
0.8432	Intermediate Similarity	NPC49196
0.8415	Intermediate Similarity	NPC472116
0.84	Intermediate Similarity	NPC326575
0.8352	Intermediate Similarity	NPC133261
0.8333	Intermediate Similarity	NPC128265
0.8333	Intermediate Similarity	NPC254240
0.8333	Intermediate Similarity	NPC264176
0.8333	Intermediate Similarity	NPC312870
0.8333	Intermediate Similarity	NPC294909
0.8333	Intermediate Similarity	NPC199851
0.8324	Intermediate Similarity	NPC50503
0.8315	Intermediate Similarity	NPC139291
0.8315	Intermediate Similarity	NPC472108
0.8287	Intermediate Similarity	NPC63199
0.8287	Intermediate Similarity	NPC102338
0.8287	Intermediate Similarity	NPC196251
0.8287	Intermediate Similarity	NPC111602
0.8261	Intermediate Similarity	NPC57994
0.8261	Intermediate Similarity	NPC289299
0.8246	Intermediate Similarity	NPC194881
0.8211	Intermediate Similarity	NPC238457
0.8162	Intermediate Similarity	NPC220151
0.8162	Intermediate Similarity	NPC19692
0.8125	Intermediate Similarity	NPC472123
0.8092	Intermediate Similarity	NPC21174
0.8092	Intermediate Similarity	NPC271797
0.8011	Intermediate Similarity	NPC159125
0.8	Intermediate Similarity	NPC469896
0.7979	Intermediate Similarity	NPC53344
0.7959	Intermediate Similarity	NPC472098
0.795	Intermediate Similarity	NPC472099
0.7919	Intermediate Similarity	NPC221100
0.7919	Intermediate Similarity	NPC234078
0.7865	Intermediate Similarity	NPC162730
0.7861	Intermediate Similarity	NPC55493
0.7849	Intermediate Similarity	NPC469501
0.7849	Intermediate Similarity	NPC469470
0.7819	Intermediate Similarity	NPC81802
0.7819	Intermediate Similarity	NPC472210
0.7819	Intermediate Similarity	NPC247735
0.7819	Intermediate Similarity	NPC472295
0.7819	Intermediate Similarity	NPC269886
0.7784	Intermediate Similarity	NPC469541
0.7772	Intermediate Similarity	NPC474116
0.7754	Intermediate Similarity	NPC329858
0.7754	Intermediate Similarity	NPC314333
0.7753	Intermediate Similarity	NPC317430
0.7747	Intermediate Similarity	NPC248462
0.7747	Intermediate Similarity	NPC219336
0.7723	Intermediate Similarity	NPC52254
0.7722	Intermediate Similarity	NPC161861
0.7713	Intermediate Similarity	NPC473763
0.7713	Intermediate Similarity	NPC117244
0.7692	Intermediate Similarity	NPC14325
0.7692	Intermediate Similarity	NPC217372
0.7692	Intermediate Similarity	NPC28848
0.7692	Intermediate Similarity	NPC15573
0.7692	Intermediate Similarity	NPC183662
0.7673	Intermediate Similarity	NPC174788
0.7656	Intermediate Similarity	NPC149708
0.7653	Intermediate Similarity	NPC472111
0.7633	Intermediate Similarity	NPC20144
0.7598	Intermediate Similarity	NPC56233
0.7596	Intermediate Similarity	NPC33949
0.7582	Intermediate Similarity	NPC329688
0.7582	Intermediate Similarity	NPC189812
0.7577	Intermediate Similarity	NPC214428
0.7565	Intermediate Similarity	NPC102008
0.7536	Intermediate Similarity	NPC21638
0.7526	Intermediate Similarity	NPC241024
0.7526	Intermediate Similarity	NPC472297
0.7526	Intermediate Similarity	NPC472296
0.7513	Intermediate Similarity	NPC469736
0.75	Intermediate Similarity	NPC82070
0.7488	Intermediate Similarity	NPC152768
0.7488	Intermediate Similarity	NPC148183
0.7488	Intermediate Similarity	NPC476114
0.7487	Intermediate Similarity	NPC472292
0.7475	Intermediate Similarity	NPC277350
0.7475	Intermediate Similarity	NPC472291
0.7456	Intermediate Similarity	NPC104483
0.7446	Intermediate Similarity	NPC121903
0.7437	Intermediate Similarity	NPC477065
0.7433	Intermediate Similarity	NPC19679
0.7432	Intermediate Similarity	NPC476425
0.7419	Intermediate Similarity	NPC91179
0.7415	Intermediate Similarity	NPC281049
0.7407	Intermediate Similarity	NPC311858
0.7405	Intermediate Similarity	NPC211997
0.7405	Intermediate Similarity	NPC145885
0.7405	Intermediate Similarity	NPC84827
0.7405	Intermediate Similarity	NPC14113
0.7404	Intermediate Similarity	NPC475271
0.7398	Intermediate Similarity	NPC249040
0.7391	Intermediate Similarity	NPC469938
0.7386	Intermediate Similarity	NPC478076
0.7377	Intermediate Similarity	NPC158129
0.7371	Intermediate Similarity	NPC472293
0.7366	Intermediate Similarity	NPC305984
0.7363	Intermediate Similarity	NPC469743
0.736	Intermediate Similarity	NPC129721
0.7354	Intermediate Similarity	NPC62510
0.7351	Intermediate Similarity	NPC134586
0.7351	Intermediate Similarity	NPC203754
0.7351	Intermediate Similarity	NPC150048
0.734	Intermediate Similarity	NPC475778
0.7337	Intermediate Similarity	NPC327592
0.7327	Intermediate Similarity	NPC234999
0.7323	Intermediate Similarity	NPC328318
0.7323	Intermediate Similarity	NPC328596
0.7322	Intermediate Similarity	NPC65080
0.7316	Intermediate Similarity	NPC62749
0.7316	Intermediate Similarity	NPC235684
0.7312	Intermediate Similarity	NPC64436
0.73	Intermediate Similarity	NPC317373
0.7292	Intermediate Similarity	NPC95783
0.7283	Intermediate Similarity	NPC126492
0.7277	Intermediate Similarity	NPC478158
0.7273	Intermediate Similarity	NPC40070
0.7273	Intermediate Similarity	NPC475506
0.7263	Intermediate Similarity	NPC113946
0.7259	Intermediate Similarity	NPC81535
0.7258	Intermediate Similarity	NPC267885
0.7258	Intermediate Similarity	NPC476441
0.7254	Intermediate Similarity	NPC129909
0.7251	Intermediate Similarity	NPC88097
0.725	Intermediate Similarity	NPC475847
0.725	Intermediate Similarity	NPC185742
0.725	Intermediate Similarity	NPC314648
0.7241	Intermediate Similarity	NPC126066
0.7236	Intermediate Similarity	NPC155143
0.7236	Intermediate Similarity	NPC476874
0.7235	Intermediate Similarity	NPC474183
0.7231	Intermediate Similarity	NPC474121
0.7216	Intermediate Similarity	NPC471386
0.7214	Intermediate Similarity	NPC474145
0.7214	Intermediate Similarity	NPC475841
0.7211	Intermediate Similarity	NPC470003
0.7211	Intermediate Similarity	NPC472294
0.7211	Intermediate Similarity	NPC228835
0.7207	Intermediate Similarity	NPC285469
0.7207	Intermediate Similarity	NPC29285
0.7204	Intermediate Similarity	NPC110500
0.7204	Intermediate Similarity	NPC149155
0.7204	Intermediate Similarity	NPC203468
0.7192	Intermediate Similarity	NPC469589
0.7191	Intermediate Similarity	NPC200743
0.7191	Intermediate Similarity	NPC281094
0.7184	Intermediate Similarity	NPC478157
0.7181	Intermediate Similarity	NPC126709
0.7181	Intermediate Similarity	NPC248041
0.7178	Intermediate Similarity	NPC314297
0.7178	Intermediate Similarity	NPC315545
0.7174	Intermediate Similarity	NPC78020
0.7172	Intermediate Similarity	NPC74413
0.7171	Intermediate Similarity	NPC318299
0.7166	Intermediate Similarity	NPC84347
0.7165	Intermediate Similarity	NPC243716
0.7157	Intermediate Similarity	NPC475422
0.7151	Intermediate Similarity	NPC473297
0.715	Intermediate Similarity	NPC260900
0.715	Intermediate Similarity	NPC57398
0.715	Intermediate Similarity	NPC470730
0.715	Intermediate Similarity	NPC477175
0.7143	Intermediate Similarity	NPC87755
0.7143	Intermediate Similarity	NPC470440
0.7136	Intermediate Similarity	NPC54744
0.7136	Intermediate Similarity	NPC317752
0.7135	Intermediate Similarity	NPC315555
0.7129	Intermediate Similarity	NPC472065

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 NPC79062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	521
0.2-0.3	627
0.3-0.4	1700
0.4-0.5	2615
0.5-0.6	2453
0.6-0.7	941
0.7-0.8	92
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8432	Intermediate Similarity	NPD4601	Approved
0.8432	Intermediate Similarity	NPD4600	Approved
0.8333	Intermediate Similarity	NPD4501	Approved
0.8333	Intermediate Similarity	NPD4500	Approved
0.828	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4602	Approved
0.8053	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7944	Discontinued
0.7754	Intermediate Similarity	NPD4499	Approved
0.7716	Intermediate Similarity	NPD4520	Approved
0.7656	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5898	Approved
0.7609	Intermediate Similarity	NPD5899	Approved
0.7609	Intermediate Similarity	NPD5897	Approved
0.7565	Intermediate Similarity	NPD4397	Phase 1
0.7565	Intermediate Similarity	NPD53	Approved
0.7565	Intermediate Similarity	NPD7778	Approved
0.7565	Intermediate Similarity	NPD7777	Approved
0.7541	Intermediate Similarity	NPD5104	Approved
0.7541	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD750	Phase 2
0.7487	Intermediate Similarity	NPD7665	Phase 2
0.7487	Intermediate Similarity	NPD7666	Phase 3
0.7473	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7233	Approved
0.7421	Intermediate Similarity	NPD7234	Approved
0.7421	Intermediate Similarity	NPD4334	Discontinued
0.7407	Intermediate Similarity	NPD5444	Phase 1
0.7387	Intermediate Similarity	NPD7001	Phase 3
0.7376	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3385	Approved
0.7348	Intermediate Similarity	NPD2915	Discontinued
0.7347	Intermediate Similarity	NPD6999	Discontinued
0.7347	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3393	Approved
0.7317	Intermediate Similarity	NPD3394	Approved
0.7317	Intermediate Similarity	NPD3389	Approved
0.7302	Intermediate Similarity	NPD7482	Phase 2
0.7302	Intermediate Similarity	NPD7483	Phase 2
0.73	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5075	Discontinued
0.7255	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8114	Approved
0.725	Intermediate Similarity	NPD8115	Approved
0.7249	Intermediate Similarity	NPD2094	Phase 2
0.7249	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2095	Phase 2
0.7249	Intermediate Similarity	NPD2092	Phase 2
0.7245	Intermediate Similarity	NPD5003	Discontinued
0.7228	Intermediate Similarity	NPD2916	Discontinued
0.7216	Intermediate Similarity	NPD4315	Phase 2
0.7214	Intermediate Similarity	NPD7568	Phase 1
0.7211	Intermediate Similarity	NPD2096	Phase 2
0.7211	Intermediate Similarity	NPD2091	Phase 2
0.7204	Intermediate Similarity	NPD482	Approved
0.7189	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5293	Phase 2
0.7182	Intermediate Similarity	NPD2511	Approved
0.7182	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6227	Discontinued
0.7172	Intermediate Similarity	NPD6248	Phase 2
0.7172	Intermediate Similarity	NPD6249	Phase 2
0.7167	Intermediate Similarity	NPD4326	Phase 2
0.7166	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5426	Phase 3
0.7158	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6206	Phase 1
0.7151	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD43	Approved
0.7151	Intermediate Similarity	NPD6182	Approved
0.715	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6479	Discontinued
0.7135	Intermediate Similarity	NPD2882	Phase 1
0.7126	Intermediate Similarity	NPD3654	Approved
0.7121	Intermediate Similarity	NPD6261	Phase 3
0.712	Intermediate Similarity	NPD6178	Phase 3
0.7115	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8325	Phase 3
0.7115	Intermediate Similarity	NPD8326	Phase 3
0.7105	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1683	Approved
0.71	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5862	Discovery
0.7081	Intermediate Similarity	NPD4640	Approved
0.7081	Intermediate Similarity	NPD4639	Approved
0.7081	Intermediate Similarity	NPD4638	Approved
0.7077	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2336	Approved
0.7073	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4547	Phase 3
0.7059	Intermediate Similarity	NPD2510	Approved
0.7059	Intermediate Similarity	NPD2509	Approved
0.7053	Intermediate Similarity	NPD5473	Discontinued
0.7051	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7957	Phase 1
0.7039	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6158	Phase 2
0.7033	Intermediate Similarity	NPD1630	Approved
0.7028	Intermediate Similarity	NPD6995	Phase 1
0.7027	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD2564	Approved
0.7026	Intermediate Similarity	NPD6281	Approved
0.7026	Intermediate Similarity	NPD2565	Phase 2
0.7019	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8408	Discontinued
0.701	Intermediate Similarity	NPD2383	Phase 1
0.701	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4948	Discontinued
0.7	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2844	Phase 3
0.6977	Remote Similarity	NPD7730	Approved
0.6977	Remote Similarity	NPD7731	Approved
0.6973	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7789	Approved
0.6972	Remote Similarity	NPD7791	Approved
0.6972	Remote Similarity	NPD7950	Approved
0.6972	Remote Similarity	NPD7952	Approved
0.6972	Remote Similarity	NPD7790	Approved
0.6972	Remote Similarity	NPD7953	Approved
0.6972	Remote Similarity	NPD7951	Approved
0.697	Remote Similarity	NPD4427	Phase 2
0.6967	Remote Similarity	NPD6770	Approved
0.6965	Remote Similarity	NPD5427	Suspended
0.6963	Remote Similarity	NPD7271	Approved
0.6961	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5505	Discontinued
0.6952	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6642	Approved
0.6947	Remote Similarity	NPD6641	Approved
0.6946	Remote Similarity	NPD6176	Phase 1
0.6946	Remote Similarity	NPD5487	Phase 1
0.6943	Remote Similarity	NPD4957	Phase 2
0.6942	Remote Similarity	NPD4506	Discontinued
0.6938	Remote Similarity	NPD4897	Phase 2
0.6936	Remote Similarity	NPD45	Approved
0.6936	Remote Similarity	NPD6554	Approved
0.6935	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2307	Discontinued
0.6935	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4047	Discontinued
0.6931	Remote Similarity	NPD7817	Phase 1
0.693	Remote Similarity	NPD7426	Phase 1
0.6927	Remote Similarity	NPD4885	Approved
0.6927	Remote Similarity	NPD4204	Approved
0.6927	Remote Similarity	NPD4203	Approved
0.6923	Remote Similarity	NPD8020	Approved
0.6923	Remote Similarity	NPD8021	Approved
0.6919	Remote Similarity	NPD1631	Approved
0.6919	Remote Similarity	NPD7878	Phase 2
0.6912	Remote Similarity	NPD7103	Approved
0.6912	Remote Similarity	NPD7824	Approved
0.6912	Remote Similarity	NPD6987	Phase 1
0.6911	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5891	Approved
0.6907	Remote Similarity	NPD5555	Phase 1
0.6905	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5913	Phase 3
0.6898	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2380	Approved
0.6895	Remote Similarity	NPD5501	Discontinued
0.6895	Remote Similarity	NPD2381	Approved
0.6895	Remote Similarity	NPD2382	Approved
0.6888	Remote Similarity	NPD6068	Discontinued
0.6885	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7618	Phase 3
0.6884	Remote Similarity	NPD7619	Phase 3
0.6875	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6452	Discontinued
0.6875	Remote Similarity	NPD7470	Discontinued
0.6872	Remote Similarity	NPD5809	Phase 3
0.6872	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD1573	Approved
0.6862	Remote Similarity	NPD1575	Approved
0.6856	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7564	Discontinued
0.685	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7935	Phase 2
0.6847	Remote Similarity	NPD7727	Phase 2
0.6845	Remote Similarity	NPD7222	Phase 2
0.6845	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7455	Approved
0.6842	Remote Similarity	NPD7454	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