NPASS Compound

Structure

CID143533 OpenBabel06191715502D 24 28 0 0 1 0 0 0 0 0999 V2000 0.5311 1.8797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0930 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7715 0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1373 -0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1375 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3531 -1.3593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7837 -2.2645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -2.7172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5689 -0.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2146 -1.3632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5686 -0.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7839 -1.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5687 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5687 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7849 -1.3587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0002 -0.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7845 0.4529 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7843 1.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7851 -2.2642 0.0000 N 0 0 3 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 -0.2854 2.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6882 1.4127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 3 12 2 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 16 2 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 15 10 1 6 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 18 22 1 0 0 0 0 19 20 1 1 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.17
Volume:	335.449
LogP:	3.137
LogD:	2.976
LogS:	-2.421
# Rotatable Bonds:	2
TPSA:	34.47
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	4.581
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	3.4908145607914776e-05
Pgp-inhibitor:	0.065
Pgp-substrate:	0.436
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.236
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	74.32386016845703%
Volume Distribution (VD):	3.002
Pgp-substrate:	27.376169204711914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.4
CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.694
CYP2D6-inhibitor:	0.23
CYP2D6-substrate:	0.698
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	11.934
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.157
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC143533

Natural Product ID:	NPC143533
*Common Name:**	NTMOAQDHNZYZMZ-QWCNWJGKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NTMOAQDHNZYZMZ-QWCNWJGKSA-N
Standard InCHI:	InChI=1S/C20H22N2O2/c1-3-12-11-21-9-8-14-13-6-4-5-7-16(13)22-18(14)17(21)10-15(12)19(22)20(23)24-2/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17-,19-/m0/s1
SMILES:	C/C=C1/CN2CCc3c4ccccc4n4c3[C@@H]2C[C@@H]1[C@H]4C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338254
PubChem CID:	5385014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003762] Pleiocarpaman 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
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12628396]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	Hairy roots	n.a.	n.a.	PMID[19271765]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26285573]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619887]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631435]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264679]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264682]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320741]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5881	Catharanthus roseus	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]
NPO5826	Alstonia plumosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9706	Ursinia trifida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5881	Catharanthus roseus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10622	Piper artanthe	Species	Piperaceae	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	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[551092]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[551092]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40000.0	nM	PMID[551092]

☑ 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 NPC143533 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	294
0.1-0.2	1719
0.2-0.3	11467
0.3-0.4	20322
0.4-0.5	3719
0.5-0.6	2582
0.6-0.7	2081
0.7-0.8	420
0.8-0.85	58
0.85-0.9	30
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9364	High Similarity	NPC472116
0.9195	High Similarity	NPC57994
0.9195	High Similarity	NPC289299
0.9006	High Similarity	NPC472119
0.8844	High Similarity	NPC472107
0.8844	High Similarity	NPC79062
0.883	High Similarity	NPC469896
0.8793	High Similarity	NPC478077
0.8786	High Similarity	NPC258480
0.8743	High Similarity	NPC472323
0.8721	High Similarity	NPC15840
0.8715	High Similarity	NPC245916
0.8701	High Similarity	NPC472097
0.8686	High Similarity	NPC66210
0.8621	High Similarity	NPC472104
0.8614	High Similarity	NPC81229
0.8614	High Similarity	NPC255229
0.8605	High Similarity	NPC234987
0.8588	High Similarity	NPC196251
0.8588	High Similarity	NPC63199
0.8588	High Similarity	NPC111602
0.8588	High Similarity	NPC175474
0.8588	High Similarity	NPC102338
0.8516	High Similarity	NPC52557
0.8452	Intermediate Similarity	NPC194881
0.8448	Intermediate Similarity	NPC219336
0.8391	Intermediate Similarity	NPC183662
0.8391	Intermediate Similarity	NPC15573
0.8391	Intermediate Similarity	NPC217372
0.8352	Intermediate Similarity	NPC113626
0.8333	Intermediate Similarity	NPC472112
0.8261	Intermediate Similarity	NPC469736
0.8242	Intermediate Similarity	NPC472113
0.8239	Intermediate Similarity	NPC133261
0.8229	Intermediate Similarity	NPC472122
0.8229	Intermediate Similarity	NPC24594
0.8226	Intermediate Similarity	NPC195461
0.8226	Intermediate Similarity	NPC128265
0.8226	Intermediate Similarity	NPC79129
0.8226	Intermediate Similarity	NPC254240
0.8226	Intermediate Similarity	NPC312870
0.8226	Intermediate Similarity	NPC313985
0.8226	Intermediate Similarity	NPC249150
0.8226	Intermediate Similarity	NPC199851
0.8226	Intermediate Similarity	NPC294909
0.8226	Intermediate Similarity	NPC49196
0.8226	Intermediate Similarity	NPC81654
0.8192	Intermediate Similarity	NPC187827
0.8192	Intermediate Similarity	NPC472105
0.8152	Intermediate Similarity	NPC220151
0.8152	Intermediate Similarity	NPC19692
0.8118	Intermediate Similarity	NPC50503
0.8105	Intermediate Similarity	NPC238457
0.8081	Intermediate Similarity	NPC21174
0.8081	Intermediate Similarity	NPC271797
0.8079	Intermediate Similarity	NPC145885
0.8079	Intermediate Similarity	NPC84827
0.8079	Intermediate Similarity	NPC14113
0.8011	Intermediate Similarity	NPC161861
0.8011	Intermediate Similarity	NPC472123
0.8	Intermediate Similarity	NPC247735
0.8	Intermediate Similarity	NPC472109
0.8	Intermediate Similarity	NPC472295
0.8	Intermediate Similarity	NPC81802
0.8	Intermediate Similarity	NPC472110
0.8	Intermediate Similarity	NPC472210
0.8	Intermediate Similarity	NPC159125
0.8	Intermediate Similarity	NPC269886
0.7978	Intermediate Similarity	NPC326575
0.7966	Intermediate Similarity	NPC469938
0.7935	Intermediate Similarity	NPC314333
0.7935	Intermediate Similarity	NPC329858
0.7892	Intermediate Similarity	NPC117244
0.7892	Intermediate Similarity	NPC473763
0.7857	Intermediate Similarity	NPC472098
0.7833	Intermediate Similarity	NPC248462
0.7833	Intermediate Similarity	NPC248041
0.7833	Intermediate Similarity	NPC126709
0.7817	Intermediate Similarity	NPC221100
0.7817	Intermediate Similarity	NPC234078
0.7802	Intermediate Similarity	NPC139291
0.7802	Intermediate Similarity	NPC472108
0.779	Intermediate Similarity	NPC91179
0.7784	Intermediate Similarity	NPC472114
0.7784	Intermediate Similarity	NPC472115
0.7771	Intermediate Similarity	NPC469541
0.7761	Intermediate Similarity	NPC472099
0.776	Intermediate Similarity	NPC57398
0.7742	Intermediate Similarity	NPC469470
0.7742	Intermediate Similarity	NPC469501
0.774	Intermediate Similarity	NPC317430
0.7735	Intermediate Similarity	NPC283219
0.7725	Intermediate Similarity	NPC20144
0.7722	Intermediate Similarity	NPC267885
0.7684	Intermediate Similarity	NPC56233
0.7677	Intermediate Similarity	NPC264176
0.7676	Intermediate Similarity	NPC62749
0.7676	Intermediate Similarity	NPC235684
0.7674	Intermediate Similarity	NPC478076
0.7668	Intermediate Similarity	NPC162730
0.7667	Intermediate Similarity	NPC203468
0.7667	Intermediate Similarity	NPC149155
0.7667	Intermediate Similarity	NPC110500
0.7662	Intermediate Similarity	NPC281049
0.766	Intermediate Similarity	NPC55493
0.766	Intermediate Similarity	NPC472292
0.7638	Intermediate Similarity	NPC472291
0.7624	Intermediate Similarity	NPC52254
0.7602	Intermediate Similarity	NPC477065
0.7585	Intermediate Similarity	NPC33949
0.7582	Intermediate Similarity	NPC14325
0.7582	Intermediate Similarity	NPC28848
0.7577	Intermediate Similarity	NPC474116
0.7568	Intermediate Similarity	NPC228835
0.7565	Intermediate Similarity	NPC214428
0.7562	Intermediate Similarity	NPC152768
0.7562	Intermediate Similarity	NPC148183
0.7561	Intermediate Similarity	NPC475271
0.7545	Intermediate Similarity	NPC104483
0.7539	Intermediate Similarity	NPC472293
0.7538	Intermediate Similarity	NPC476098
0.7527	Intermediate Similarity	NPC134586
0.7525	Intermediate Similarity	NPC478158
0.7513	Intermediate Similarity	NPC53344
0.75	Intermediate Similarity	NPC118940
0.75	Intermediate Similarity	NPC321708
0.7487	Intermediate Similarity	NPC94752
0.7486	Intermediate Similarity	NPC211997
0.7462	Intermediate Similarity	NPC277350
0.7459	Intermediate Similarity	NPC158129
0.7447	Intermediate Similarity	NPC17059
0.7444	Intermediate Similarity	NPC78020
0.7443	Intermediate Similarity	NPC129721
0.7432	Intermediate Similarity	NPC121903
0.7426	Intermediate Similarity	NPC478157
0.7423	Intermediate Similarity	NPC472297
0.7423	Intermediate Similarity	NPC472296
0.7423	Intermediate Similarity	NPC123395
0.7418	Intermediate Similarity	NPC477976
0.7411	Intermediate Similarity	NPC132539
0.7411	Intermediate Similarity	NPC473376
0.7409	Intermediate Similarity	NPC141454
0.7409	Intermediate Similarity	NPC262898
0.7402	Intermediate Similarity	NPC82070
0.7402	Intermediate Similarity	NPC174788
0.7391	Intermediate Similarity	NPC111275
0.7391	Intermediate Similarity	NPC64436
0.7389	Intermediate Similarity	NPC476114
0.7376	Intermediate Similarity	NPC54744
0.7371	Intermediate Similarity	NPC281094
0.7371	Intermediate Similarity	NPC149708
0.7358	Intermediate Similarity	NPC179701
0.7356	Intermediate Similarity	NPC40070
0.7356	Intermediate Similarity	NPC21638
0.7353	Intermediate Similarity	NPC305984
0.7351	Intermediate Similarity	NPC11126
0.7351	Intermediate Similarity	NPC213468
0.734	Intermediate Similarity	NPC133003
0.7337	Intermediate Similarity	NPC203754
0.7337	Intermediate Similarity	NPC150048
0.7337	Intermediate Similarity	NPC88097
0.7337	Intermediate Similarity	NPC84347
0.7333	Intermediate Similarity	NPC241024
0.7327	Intermediate Similarity	NPC318299
0.7323	Intermediate Similarity	NPC327592
0.7316	Intermediate Similarity	NPC213629
0.7313	Intermediate Similarity	NPC234999
0.731	Intermediate Similarity	NPC476874
0.7303	Intermediate Similarity	NPC221786
0.7303	Intermediate Similarity	NPC474880
0.7292	Intermediate Similarity	NPC471386
0.7291	Intermediate Similarity	NPC317752
0.7288	Intermediate Similarity	NPC285469
0.7286	Intermediate Similarity	NPC317373
0.7283	Intermediate Similarity	NPC329688
0.7283	Intermediate Similarity	NPC189812
0.7282	Intermediate Similarity	NPC171317
0.7273	Intermediate Similarity	NPC165599
0.7263	Intermediate Similarity	NPC229173
0.7258	Intermediate Similarity	NPC55772
0.7255	Intermediate Similarity	NPC477979
0.725	Intermediate Similarity	NPC54420
0.7245	Intermediate Similarity	NPC293917
0.7245	Intermediate Similarity	NPC81535
0.7241	Intermediate Similarity	NPC75634
0.7241	Intermediate Similarity	NPC475778
0.7232	Intermediate Similarity	NPC473297
0.7225	Intermediate Similarity	NPC470440
0.7225	Intermediate Similarity	NPC64216
0.7222	Intermediate Similarity	NPC328596
0.7222	Intermediate Similarity	NPC328318
0.722	Intermediate Similarity	NPC36405
0.7214	Intermediate Similarity	NPC266249
0.7213	Intermediate Similarity	NPC65080
0.7211	Intermediate Similarity	NPC311858
0.7208	Intermediate Similarity	NPC249040
0.72	Intermediate Similarity	NPC472065
0.72	Intermediate Similarity	NPC472111
0.7198	Intermediate Similarity	NPC49954
0.7198	Intermediate Similarity	NPC474561

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 NPC143533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	491
0.2-0.3	736
0.3-0.4	1554
0.4-0.5	2398
0.5-0.6	2574
0.6-0.7	1065
0.7-0.8	144
0.8-0.85	11
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9195	High Similarity	NPD4602	Approved
0.8556	High Similarity	NPD4520	Approved
0.8246	Intermediate Similarity	NPD2915	Discontinued
0.8229	Intermediate Similarity	NPD5104	Approved
0.8226	Intermediate Similarity	NPD4500	Approved
0.8226	Intermediate Similarity	NPD4600	Approved
0.8226	Intermediate Similarity	NPD4501	Approved
0.8226	Intermediate Similarity	NPD4601	Approved
0.8075	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD750	Phase 2
0.7953	Intermediate Similarity	NPD4326	Phase 2
0.7935	Intermediate Similarity	NPD4499	Approved
0.7926	Intermediate Similarity	NPD4397	Phase 1
0.7926	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD5075	Discontinued
0.7853	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD482	Approved
0.7663	Intermediate Similarity	NPD7482	Phase 2
0.7663	Intermediate Similarity	NPD7483	Phase 2
0.7624	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2095	Phase 2
0.7609	Intermediate Similarity	NPD2092	Phase 2
0.7609	Intermediate Similarity	NPD2094	Phase 2
0.7596	Intermediate Similarity	NPD6452	Discontinued
0.7581	Intermediate Similarity	NPD5809	Phase 3
0.7579	Intermediate Similarity	NPD7944	Discontinued
0.7568	Intermediate Similarity	NPD2091	Phase 2
0.7568	Intermediate Similarity	NPD2096	Phase 2
0.7563	Intermediate Similarity	NPD7665	Phase 2
0.7563	Intermediate Similarity	NPD7666	Phase 3
0.75	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6178	Phase 3
0.7455	Intermediate Similarity	NPD3385	Approved
0.7432	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6999	Discontinued
0.7421	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5897	Approved
0.7405	Intermediate Similarity	NPD5899	Approved
0.7405	Intermediate Similarity	NPD5898	Approved
0.7401	Intermediate Similarity	NPD1630	Approved
0.7389	Intermediate Similarity	NPD3389	Approved
0.7389	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3393	Approved
0.7389	Intermediate Similarity	NPD3394	Approved
0.7366	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7103	Approved
0.732	Intermediate Similarity	NPD5003	Discontinued
0.7316	Intermediate Similarity	NPD7234	Approved
0.7316	Intermediate Similarity	NPD7233	Approved
0.7313	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7001	Phase 3
0.7278	Intermediate Similarity	NPD1631	Approved
0.7277	Intermediate Similarity	NPD7470	Discontinued
0.7268	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2844	Phase 3
0.7249	Intermediate Similarity	NPD6227	Discontinued
0.7245	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8115	Approved
0.7236	Intermediate Similarity	NPD8114	Approved
0.7228	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4334	Discontinued
0.7213	Intermediate Similarity	NPD1573	Approved
0.7213	Intermediate Similarity	NPD1575	Approved
0.7212	Intermediate Similarity	NPD3654	Approved
0.7211	Intermediate Similarity	NPD5444	Phase 1
0.7204	Intermediate Similarity	NPD7730	Approved
0.7204	Intermediate Similarity	NPD7731	Approved
0.7202	Intermediate Similarity	NPD6665	Discontinued
0.7202	Intermediate Similarity	NPD5505	Discontinued
0.72	Intermediate Similarity	NPD7568	Phase 1
0.7196	Intermediate Similarity	NPD7952	Approved
0.7196	Intermediate Similarity	NPD7791	Approved
0.7196	Intermediate Similarity	NPD7953	Approved
0.7196	Intermediate Similarity	NPD7950	Approved
0.7196	Intermediate Similarity	NPD7789	Approved
0.7196	Intermediate Similarity	NPD7951	Approved
0.7196	Intermediate Similarity	NPD7790	Approved
0.7194	Intermediate Similarity	NPD7777	Approved
0.7194	Intermediate Similarity	NPD53	Approved
0.7194	Intermediate Similarity	NPD7778	Approved
0.7192	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7271	Approved
0.7186	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1683	Approved
0.7179	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4948	Discontinued
0.7158	Intermediate Similarity	NPD5862	Discovery
0.7151	Intermediate Similarity	NPD5020	Approved
0.715	Intermediate Similarity	NPD2336	Approved
0.715	Intermediate Similarity	NPD5426	Phase 3
0.715	Intermediate Similarity	NPD6987	Phase 1
0.7143	Intermediate Similarity	NPD4547	Phase 3
0.7136	Intermediate Similarity	NPD7824	Approved
0.7135	Intermediate Similarity	NPD4804	Approved
0.7128	Intermediate Similarity	NPD4427	Phase 2
0.7128	Intermediate Similarity	NPD7618	Phase 3
0.7128	Intermediate Similarity	NPD7619	Phase 3
0.7119	Intermediate Similarity	NPD2882	Phase 1
0.7114	Intermediate Similarity	NPD7957	Phase 1
0.7114	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6281	Approved
0.7098	Intermediate Similarity	NPD2565	Phase 2
0.7098	Intermediate Similarity	NPD2564	Approved
0.7097	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD5017	Discontinued
0.7079	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2896	Discontinued
0.707	Intermediate Similarity	NPD4885	Approved
0.7065	Intermediate Similarity	NPD4638	Approved
0.7065	Intermediate Similarity	NPD4640	Approved
0.7065	Intermediate Similarity	NPD4639	Approved
0.7065	Intermediate Similarity	NPD5901	Discontinued
0.7062	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4918	Discontinued
0.7052	Intermediate Similarity	NPD4805	Approved
0.7051	Intermediate Similarity	NPD5891	Approved
0.7049	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2916	Discontinued
0.7039	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5473	Discontinued
0.7035	Intermediate Similarity	NPD6479	Discontinued
0.7033	Intermediate Similarity	NPD6770	Approved
0.7027	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4315	Phase 2
0.7023	Intermediate Similarity	NPD7688	Phase 1
0.7022	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6158	Phase 2
0.7021	Intermediate Similarity	NPD2144	Approved
0.7018	Intermediate Similarity	NPD6554	Approved
0.7018	Intermediate Similarity	NPD45	Approved
0.7011	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4047	Discontinued
0.7005	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1586	Approved
0.7005	Intermediate Similarity	NPD2307	Discontinued
0.7	Intermediate Similarity	NPD7817	Phase 1
0.7	Intermediate Similarity	NPD7727	Phase 2
0.7	Intermediate Similarity	NPD3038	Discontinued
0.6995	Remote Similarity	NPD2383	Phase 1
0.6995	Remote Similarity	NPD3961	Discontinued
0.6995	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3583	Phase 2
0.6991	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6248	Phase 2
0.6985	Remote Similarity	NPD6249	Phase 2
0.6973	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6206	Phase 1
0.6968	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2510	Approved
0.6961	Remote Similarity	NPD2509	Approved
0.6959	Remote Similarity	NPD1534	Approved
0.6954	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD43	Approved
0.6952	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6182	Approved
0.695	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5475	Discontinued
0.6938	Remote Similarity	NPD8325	Phase 3
0.6938	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8326	Phase 3
0.6935	Remote Similarity	NPD6261	Phase 3
0.6935	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8356	Approved
0.6934	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7111	Discontinued
0.6931	Remote Similarity	NPD8072	Approved
0.693	Remote Similarity	NPD7781	Approved
0.693	Remote Similarity	NPD7780	Approved
0.6927	Remote Similarity	NPD7564	Discontinued
0.6923	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7599	Phase 2
0.6923	Remote Similarity	NPD5255	Approved
0.6919	Remote Similarity	NPD5512	Phase 3
0.6908	Remote Similarity	NPD7454	Approved
0.6908	Remote Similarity	NPD7455	Approved
0.6897	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8272	Phase 2
0.6897	Remote Similarity	NPD6323	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data