NPASS Compound

Structure

CID14325 OpenBabel06191715342D 25 29 0 0 1 0 0 0 0 0999 V2000 1.7210 2.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 2.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3966 -0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3968 0.9681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5567 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5571 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8775 -0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1985 -0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7169 -0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0378 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 1.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6799 0.9694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7171 0.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3590 0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0380 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5189 -0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8779 1.4532 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3588 -0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5187 -1.4851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8803 1.4783 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 2 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 16 2 0 0 0 0 7 11 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 8 17 2 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 2 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.12
Volume:	336.33
LogP:	3.107
LogD:	2.437
LogS:	-6.136
# Rotatable Bonds:	1
TPSA:	61.19
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	3.282
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.904
MDCK Permeability:	2.978856355184689e-05
Pgp-inhibitor:	0.155
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	87.0645980834961%
Volume Distribution (VD):	1.199
Pgp-substrate:	7.235928058624268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.904
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.529
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	6.7
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.252
AMES Toxicity:	0.843
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.041
Carcinogencity:	0.361
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC14325

Natural Product ID:	NPC14325
*Common Name:**	PEZXVOHRDBYBFR-CYBMUJFWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PEZXVOHRDBYBFR-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C20H16N2O3/c1-2-13-14-8-17-18-12(7-11-5-3-4-6-16(11)21-18)9-22(17)19(23)15(14)10-25-20(13)24/h3-8,13H,2,9-10H2,1H3/t13-/m1/s1
SMILES:	CC[C@@H]1c2cc3-c4c(cc5ccccc5n4)Cn3c(=O)c2COC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL71339
PubChem CID:	169724
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002111] Pyranopyridines

*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
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21348469]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3735324]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	590.0	nM	PMID[542152]

☑ 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 NPC14325 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	358
0.1-0.2	2378
0.2-0.3	10098
0.3-0.4	10962
0.4-0.5	13676
0.5-0.6	2746
0.6-0.7	2066
0.7-0.8	390
0.8-0.85	12
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28848
0.9458	High Similarity	NPC311858
0.9235	High Similarity	NPC129909
0.8895	High Similarity	NPC61435
0.8882	High Similarity	NPC470003
0.887	High Similarity	NPC192674
0.8263	Intermediate Similarity	NPC74562
0.8263	Intermediate Similarity	NPC316181
0.8263	Intermediate Similarity	NPC151781
0.8081	Intermediate Similarity	NPC65080
0.8012	Intermediate Similarity	NPC238499
0.801	Intermediate Similarity	NPC128115
0.7989	Intermediate Similarity	NPC245916
0.7964	Intermediate Similarity	NPC281094
0.7958	Intermediate Similarity	NPC477548
0.7865	Intermediate Similarity	NPC24864
0.7838	Intermediate Similarity	NPC19692
0.7838	Intermediate Similarity	NPC220151
0.7826	Intermediate Similarity	NPC55493
0.7771	Intermediate Similarity	NPC478186
0.776	Intermediate Similarity	NPC111602
0.776	Intermediate Similarity	NPC102338
0.776	Intermediate Similarity	NPC63199
0.776	Intermediate Similarity	NPC196251
0.7747	Intermediate Similarity	NPC66210
0.7746	Intermediate Similarity	NPC478182
0.7744	Intermediate Similarity	NPC277157
0.7735	Intermediate Similarity	NPC472119
0.7711	Intermediate Similarity	NPC470440
0.7692	Intermediate Similarity	NPC472107
0.7692	Intermediate Similarity	NPC79062
0.7688	Intermediate Similarity	NPC194881
0.768	Intermediate Similarity	NPC472104
0.7657	Intermediate Similarity	NPC470509
0.7637	Intermediate Similarity	NPC258480
0.7632	Intermediate Similarity	NPC199851
0.7632	Intermediate Similarity	NPC312870
0.7632	Intermediate Similarity	NPC294909
0.7632	Intermediate Similarity	NPC254240
0.7632	Intermediate Similarity	NPC128265
0.7594	Intermediate Similarity	NPC198673
0.7582	Intermediate Similarity	NPC143533
0.7581	Intermediate Similarity	NPC472097
0.7579	Intermediate Similarity	NPC241024
0.7572	Intermediate Similarity	NPC293487
0.7568	Intermediate Similarity	NPC175474
0.7556	Intermediate Similarity	NPC234987
0.7543	Intermediate Similarity	NPC478184
0.754	Intermediate Similarity	NPC472113
0.7527	Intermediate Similarity	NPC314333
0.7526	Intermediate Similarity	NPC277350
0.7526	Intermediate Similarity	NPC168911
0.7486	Intermediate Similarity	NPC161861
0.7485	Intermediate Similarity	NPC20144
0.7459	Intermediate Similarity	NPC326575
0.7458	Intermediate Similarity	NPC478183
0.7446	Intermediate Similarity	NPC21429
0.7443	Intermediate Similarity	NPC8104
0.7436	Intermediate Similarity	NPC238457
0.7435	Intermediate Similarity	NPC239954
0.7435	Intermediate Similarity	NPC52557
0.7433	Intermediate Similarity	NPC472112
0.7429	Intermediate Similarity	NPC81229
0.7429	Intermediate Similarity	NPC255229
0.7419	Intermediate Similarity	NPC472323
0.7418	Intermediate Similarity	NPC12649
0.741	Intermediate Similarity	NPC104483
0.7405	Intermediate Similarity	NPC133003
0.7403	Intermediate Similarity	NPC472122
0.7403	Intermediate Similarity	NPC24594
0.7386	Intermediate Similarity	NPC478185
0.7377	Intermediate Similarity	NPC15840
0.7374	Intermediate Similarity	NPC32534
0.7374	Intermediate Similarity	NPC91895
0.7371	Intermediate Similarity	NPC295898
0.7366	Intermediate Similarity	NPC141612
0.7366	Intermediate Similarity	NPC17273
0.7366	Intermediate Similarity	NPC135601
0.7358	Intermediate Similarity	NPC214428
0.7345	Intermediate Similarity	NPC21174
0.7345	Intermediate Similarity	NPC271797
0.734	Intermediate Similarity	NPC329858
0.7337	Intermediate Similarity	NPC113626
0.733	Intermediate Similarity	NPC472116
0.733	Intermediate Similarity	NPC79356
0.733	Intermediate Similarity	NPC102592
0.7326	Intermediate Similarity	NPC243756
0.732	Intermediate Similarity	NPC471944
0.7314	Intermediate Similarity	NPC299594
0.7313	Intermediate Similarity	NPC477979
0.7312	Intermediate Similarity	NPC280290
0.73	Intermediate Similarity	NPC264176
0.7297	Intermediate Similarity	NPC470205
0.7283	Intermediate Similarity	NPC187827
0.7283	Intermediate Similarity	NPC472105
0.7283	Intermediate Similarity	NPC91179
0.7282	Intermediate Similarity	NPC162730
0.7273	Intermediate Similarity	NPC478077
0.7268	Intermediate Similarity	NPC195461
0.7268	Intermediate Similarity	NPC81654
0.7268	Intermediate Similarity	NPC249150
0.7268	Intermediate Similarity	NPC79129
0.7268	Intermediate Similarity	NPC313985
0.7268	Intermediate Similarity	NPC49196
0.7258	Intermediate Similarity	NPC228835
0.7254	Intermediate Similarity	NPC212213
0.7253	Intermediate Similarity	NPC469938
0.7222	Intermediate Similarity	NPC474905
0.722	Intermediate Similarity	NPC472099
0.7214	Intermediate Similarity	NPC472098
0.7213	Intermediate Similarity	NPC84347
0.7204	Intermediate Similarity	NPC472110
0.7204	Intermediate Similarity	NPC472109
0.7204	Intermediate Similarity	NPC472108
0.7204	Intermediate Similarity	NPC139291
0.7198	Intermediate Similarity	NPC472123
0.7194	Intermediate Similarity	NPC474116
0.7189	Intermediate Similarity	NPC469896
0.7188	Intermediate Similarity	NPC474121
0.7184	Intermediate Similarity	NPC122106
0.7178	Intermediate Similarity	NPC221100
0.7178	Intermediate Similarity	NPC234078
0.7174	Intermediate Similarity	NPC211997
0.7173	Intermediate Similarity	NPC472292
0.7169	Intermediate Similarity	NPC198988
0.7167	Intermediate Similarity	NPC56233
0.7167	Intermediate Similarity	NPC114637
0.7165	Intermediate Similarity	NPC50503
0.716	Intermediate Similarity	NPC59084
0.7151	Intermediate Similarity	NPC271734
0.7136	Intermediate Similarity	NPC243850
0.7135	Intermediate Similarity	NPC247735
0.7135	Intermediate Similarity	NPC472210
0.7135	Intermediate Similarity	NPC11126
0.7135	Intermediate Similarity	NPC472295
0.7135	Intermediate Similarity	NPC81802
0.7135	Intermediate Similarity	NPC269886
0.7128	Intermediate Similarity	NPC282103
0.7127	Intermediate Similarity	NPC317430
0.712	Intermediate Similarity	NPC117244
0.712	Intermediate Similarity	NPC134586
0.712	Intermediate Similarity	NPC473763
0.7118	Intermediate Similarity	NPC63157
0.7118	Intermediate Similarity	NPC473868
0.7108	Intermediate Similarity	NPC152768
0.7108	Intermediate Similarity	NPC148183
0.7102	Intermediate Similarity	NPC470507
0.7101	Intermediate Similarity	NPC88097
0.71	Intermediate Similarity	NPC287208
0.7098	Intermediate Similarity	NPC57994
0.7098	Intermediate Similarity	NPC289299
0.7097	Intermediate Similarity	NPC73994
0.7079	Intermediate Similarity	NPC475990
0.7077	Intermediate Similarity	NPC474916
0.7071	Intermediate Similarity	NPC476115
0.7069	Intermediate Similarity	NPC37548
0.7068	Intermediate Similarity	NPC469501
0.7068	Intermediate Similarity	NPC469470
0.7068	Intermediate Similarity	NPC324091
0.7065	Intermediate Similarity	NPC469529
0.7065	Intermediate Similarity	NPC174758
0.7065	Intermediate Similarity	NPC174672
0.7062	Intermediate Similarity	NPC472293
0.7056	Intermediate Similarity	NPC469541
0.7049	Intermediate Similarity	NPC126492
0.7043	Intermediate Similarity	NPC133261
0.7043	Intermediate Similarity	NPC248462
0.7041	Intermediate Similarity	NPC472297
0.7041	Intermediate Similarity	NPC472296
0.7039	Intermediate Similarity	NPC82070
0.7035	Intermediate Similarity	NPC242556
0.703	Intermediate Similarity	NPC123839
0.7029	Intermediate Similarity	NPC40070
0.7024	Intermediate Similarity	NPC325252
0.7015	Intermediate Similarity	NPC82548
0.7011	Intermediate Similarity	NPC21605
0.7005	Intermediate Similarity	NPC88110
0.7005	Intermediate Similarity	NPC61011
0.7005	Intermediate Similarity	NPC52254
0.7	Intermediate Similarity	NPC21638
0.7	Intermediate Similarity	NPC314855
0.7	Intermediate Similarity	NPC90415
0.7	Intermediate Similarity	NPC313796
0.7	Intermediate Similarity	NPC315638
0.7	Intermediate Similarity	NPC94752
0.7	Intermediate Similarity	NPC313345
0.6994	Remote Similarity	NPC469525
0.699	Remote Similarity	NPC102008
0.6989	Remote Similarity	NPC83774
0.6981	Remote Similarity	NPC471762
0.6981	Remote Similarity	NPC66777
0.6973	Remote Similarity	NPC329688
0.6973	Remote Similarity	NPC189812
0.6971	Remote Similarity	NPC187951
0.697	Remote Similarity	NPC300183
0.6968	Remote Similarity	NPC275292
0.6968	Remote Similarity	NPC243381
0.6966	Remote Similarity	NPC51054
0.6966	Remote Similarity	NPC469536
0.6965	Remote Similarity	NPC314297

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 NPC14325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	616
0.2-0.3	789
0.3-0.4	1353
0.4-0.5	2706
0.5-0.6	2318
0.6-0.7	1001
0.7-0.8	120
0.8-0.85	8
0.85-0.9	10
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9458	High Similarity	NPD5444	Phase 1
0.9235	High Similarity	NPD3785	Clinical (unspecified phase)
0.9118	High Similarity	NPD4334	Discontinued
0.8971	High Similarity	NPD6206	Phase 1
0.892	High Similarity	NPD6261	Phase 3
0.887	High Similarity	NPD6248	Phase 2
0.887	High Similarity	NPD3800	Clinical (unspecified phase)
0.887	High Similarity	NPD6249	Phase 2
0.8851	High Similarity	NPD4315	Phase 2
0.882	High Similarity	NPD5427	Suspended
0.8674	High Similarity	NPD5487	Phase 1
0.8579	High Similarity	NPD4901	Clinical (unspecified phase)
0.8571	High Similarity	NPD3777	Phase 3
0.8443	Intermediate Similarity	NPD2915	Discontinued
0.8421	Intermediate Similarity	NPD5104	Approved
0.8307	Intermediate Similarity	NPD7573	Discontinued
0.822	Intermediate Similarity	NPD4897	Phase 2
0.8201	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5835	Phase 3
0.8148	Intermediate Similarity	NPD5834	Phase 3
0.809	Intermediate Similarity	NPD5075	Discontinued
0.8083	Intermediate Similarity	NPD7218	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD5506	Approved
0.797	Intermediate Similarity	NPD5507	Approved
0.7744	Intermediate Similarity	NPD5020	Approved
0.7713	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4500	Approved
0.7632	Intermediate Similarity	NPD4501	Approved
0.7621	Intermediate Similarity	NPD7796	Approved
0.7621	Intermediate Similarity	NPD7797	Approved
0.7528	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4499	Approved
0.7487	Intermediate Similarity	NPD5293	Phase 2
0.7459	Intermediate Similarity	NPD5809	Phase 3
0.7446	Intermediate Similarity	NPD7482	Phase 2
0.7446	Intermediate Similarity	NPD7483	Phase 2
0.7423	Intermediate Similarity	NPD3385	Approved
0.7423	Intermediate Similarity	NPD6176	Phase 1
0.7414	Intermediate Similarity	NPD4326	Phase 2
0.7405	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2882	Phase 1
0.734	Intermediate Similarity	NPD3321	Discontinued
0.7287	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5898	Approved
0.7283	Intermediate Similarity	NPD5899	Approved
0.7283	Intermediate Similarity	NPD5897	Approved
0.7278	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4601	Approved
0.7268	Intermediate Similarity	NPD4600	Approved
0.7249	Intermediate Similarity	NPD6281	Approved
0.7245	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4638	Approved
0.7222	Intermediate Similarity	NPD4640	Approved
0.7222	Intermediate Similarity	NPD4639	Approved
0.7213	Intermediate Similarity	NPD4075	Phase 2
0.7186	Intermediate Similarity	NPD2509	Approved
0.7186	Intermediate Similarity	NPD2510	Approved
0.7179	Intermediate Similarity	NPD6479	Discontinued
0.7178	Intermediate Similarity	NPD3654	Approved
0.7173	Intermediate Similarity	NPD5505	Discontinued
0.7164	Intermediate Similarity	NPD5475	Discontinued
0.7135	Intermediate Similarity	NPD2511	Approved
0.7128	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5555	Phase 1
0.712	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5003	Discontinued
0.7111	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3393	Approved
0.7108	Intermediate Similarity	NPD3394	Approved
0.7108	Intermediate Similarity	NPD3389	Approved
0.7104	Intermediate Similarity	NPD43	Approved
0.7104	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6182	Approved
0.7098	Intermediate Similarity	NPD4602	Approved
0.7076	Intermediate Similarity	NPD4047	Discontinued
0.7059	Intermediate Similarity	NPD4203	Approved
0.7059	Intermediate Similarity	NPD4204	Approved
0.7056	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3961	Discontinued
0.7039	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3947	Discontinued
0.7027	Intermediate Similarity	NPD5501	Discontinued
0.7027	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5473	Discontinued
0.7	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5400	Approved
0.7	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7010	Phase 3
0.699	Remote Similarity	NPD53	Approved
0.699	Remote Similarity	NPD7777	Approved
0.699	Remote Similarity	NPD7778	Approved
0.6989	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6158	Phase 2
0.6986	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7564	Discontinued
0.6982	Remote Similarity	NPD45	Approved
0.6982	Remote Similarity	NPD6554	Approved
0.6978	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7727	Phase 2
0.697	Remote Similarity	NPD7817	Phase 1
0.6965	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6999	Discontinued
0.6954	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1683	Approved
0.6952	Remote Similarity	NPD3078	Approved
0.6952	Remote Similarity	NPD3077	Approved
0.6952	Remote Similarity	NPD3079	Approved
0.6952	Remote Similarity	NPD4076	Approved
0.6952	Remote Similarity	NPD4079	Approved
0.6952	Remote Similarity	NPD3076	Approved
0.695	Remote Similarity	NPD8115	Approved
0.695	Remote Similarity	NPD8114	Approved
0.6946	Remote Similarity	NPD5072	Discontinued
0.6943	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4463	Approved
0.6932	Remote Similarity	NPD4462	Approved
0.6931	Remote Similarity	NPD7666	Phase 3
0.6931	Remote Similarity	NPD7665	Phase 2
0.6927	Remote Similarity	NPD2581	Approved
0.6927	Remote Similarity	NPD2582	Approved
0.6923	Remote Similarity	NPD7944	Discontinued
0.6923	Remote Similarity	NPD7619	Phase 3
0.6923	Remote Similarity	NPD7404	Approved
0.6923	Remote Similarity	NPD7618	Phase 3
0.6919	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6452	Discontinued
0.6914	Remote Similarity	NPD4547	Phase 3
0.6912	Remote Similarity	NPD7470	Discontinued
0.691	Remote Similarity	NPD6285	Phase 2
0.6908	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6771	Discontinued
0.6904	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5513	Phase 2
0.6898	Remote Similarity	NPD3505	Approved
0.6898	Remote Similarity	NPD3506	Approved
0.6893	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2565	Phase 2
0.6891	Remote Similarity	NPD2564	Approved
0.6888	Remote Similarity	NPD6550	Discontinued
0.6887	Remote Similarity	NPD8289	Discontinued
0.6885	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD200	Phase 2
0.6882	Remote Similarity	NPD201	Phase 2
0.6875	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7878	Phase 2
0.6875	Remote Similarity	NPD4948	Discontinued
0.6875	Remote Similarity	NPD4988	Discontinued
0.6872	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6395	Phase 2
0.6869	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6227	Discontinued
0.6857	Remote Similarity	NPD7469	Discontinued
0.6856	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7234	Approved
0.6839	Remote Similarity	NPD7233	Approved
0.6833	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7001	Phase 3
0.6827	Remote Similarity	NPD8326	Phase 3
0.6827	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD8325	Phase 3
0.6826	Remote Similarity	NPD3476	Approved
0.6826	Remote Similarity	NPD3475	Approved
0.6825	Remote Similarity	NPD6514	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6515	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4376	Phase 3
0.6818	Remote Similarity	NPD4397	Phase 1
0.6809	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6642	Approved
0.6809	Remote Similarity	NPD6641	Approved
0.6806	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4957	Phase 2
0.6802	Remote Similarity	NPD5512	Phase 3
0.6796	Remote Similarity	NPD1630	Approved
0.6793	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7717	Approved
0.6792	Remote Similarity	NPD7716	Approved
0.6791	Remote Similarity	NPD6492	Phase 2
0.6791	Remote Similarity	NPD5065	Approved
0.6788	Remote Similarity	NPD3390	Phase 2
0.6788	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4528	Approved
0.6786	Remote Similarity	NPD4526	Approved
0.6786	Remote Similarity	NPD4529	Approved
0.6784	Remote Similarity	NPD7308	Discontinued
0.6782	Remote Similarity	NPD2006	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