NPASS Compound

Structure

NPC471323 OpenBabel07101718312D 28 28 0 0 0 0 0 0 0 0999 V2000 -13.8564 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 24 26 2 3 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.31
Volume:	441.495
LogP:	6.686
LogD:	4.348
LogS:	-2.72
# Rotatable Bonds:	19
TPSA:	51.22
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	2.278
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	2.987900370499119e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.697
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.83
Plasma Protein Binding (PPB):	97.73504638671875%
Volume Distribution (VD):	1.235
Pgp-substrate:	1.1613409519195557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.414
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.702
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.38
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	5.048
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.864
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.96
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.779

Download Data

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

Natural Product: NPC471323

Natural Product ID:	NPC471323
*Common Name:**	Pyridin-3-Ylmethyl N-[(Z)-Heptadec-8-Enyl]Carbamate
IUPAC Name:	pyridin-3-ylmethyl N-[(Z)-heptadec-8-enyl]carbamate
Synonyms:
Standard InCHIKey:	OQYCMOCYWBHSFE-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C24H40N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-26-24(27)28-22-23-18-17-19-25-21-23/h9-10,17-19,21H,2-8,11-16,20,22H2,1H3,(H,26,27)/b10-9-
SMILES:	CCCCCCCCC=CCCCCCCCNC(=O)OCC1=CN=CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413181
PubChem CID:	71770553
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives

*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
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932133]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23891163]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24972328]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33320645]
NPO18988	Lepidium meyenii	Species	Brassicaceae	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	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	=	153.0	nM	PMID[522306]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	=	59.6	nM	PMID[522306]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Imax	=	100.0	%	PMID[522306]

☑ 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 NPC471323 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	228
0.1-0.2	3037
0.2-0.3	13607
0.3-0.4	16011
0.4-0.5	5834
0.5-0.6	2765
0.6-0.7	1103
0.7-0.8	102
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8613	High Similarity	NPC212125
0.8478	Intermediate Similarity	NPC165370
0.8392	Intermediate Similarity	NPC29702
0.8345	Intermediate Similarity	NPC471313
0.8345	Intermediate Similarity	NPC471311
0.8345	Intermediate Similarity	NPC306397
0.8105	Intermediate Similarity	NPC107287
0.7961	Intermediate Similarity	NPC112741
0.7929	Intermediate Similarity	NPC290094
0.7838	Intermediate Similarity	NPC471312
0.7778	Intermediate Similarity	NPC89490
0.7764	Intermediate Similarity	NPC98187
0.7762	Intermediate Similarity	NPC169625
0.7762	Intermediate Similarity	NPC202957
0.774	Intermediate Similarity	NPC256893
0.774	Intermediate Similarity	NPC471322
0.7724	Intermediate Similarity	NPC329896
0.7724	Intermediate Similarity	NPC475090
0.7724	Intermediate Similarity	NPC475105
0.7722	Intermediate Similarity	NPC138018
0.7707	Intermediate Similarity	NPC263455
0.7702	Intermediate Similarity	NPC471178
0.7688	Intermediate Similarity	NPC71079
0.764	Intermediate Similarity	NPC474217
0.7626	Intermediate Similarity	NPC297486
0.7626	Intermediate Similarity	NPC240136
0.7626	Intermediate Similarity	NPC471402
0.7619	Intermediate Similarity	NPC324611
0.7597	Intermediate Similarity	NPC167400
0.7593	Intermediate Similarity	NPC85918
0.7551	Intermediate Similarity	NPC315320
0.7546	Intermediate Similarity	NPC108469
0.7546	Intermediate Similarity	NPC278366
0.7546	Intermediate Similarity	NPC127730
0.7533	Intermediate Similarity	NPC328029
0.7532	Intermediate Similarity	NPC159630
0.7532	Intermediate Similarity	NPC230085
0.7531	Intermediate Similarity	NPC473057
0.75	Intermediate Similarity	NPC27802
0.75	Intermediate Similarity	NPC476322
0.7469	Intermediate Similarity	NPC471177
0.7469	Intermediate Similarity	NPC124542
0.7469	Intermediate Similarity	NPC59779
0.745	Intermediate Similarity	NPC322488
0.7448	Intermediate Similarity	NPC151489
0.7427	Intermediate Similarity	NPC284559
0.7423	Intermediate Similarity	NPC97367
0.7421	Intermediate Similarity	NPC312860
0.7413	Intermediate Similarity	NPC265605
0.7413	Intermediate Similarity	NPC48564
0.7413	Intermediate Similarity	NPC182570
0.741	Intermediate Similarity	NPC249614
0.7407	Intermediate Similarity	NPC76540
0.7394	Intermediate Similarity	NPC319456
0.7381	Intermediate Similarity	NPC134586
0.7368	Intermediate Similarity	NPC114310
0.7337	Intermediate Similarity	NPC211997
0.7324	Intermediate Similarity	NPC91958
0.7317	Intermediate Similarity	NPC263439
0.731	Intermediate Similarity	NPC470474
0.7288	Intermediate Similarity	NPC289786
0.7283	Intermediate Similarity	NPC475835
0.7273	Intermediate Similarity	NPC477975
0.7256	Intermediate Similarity	NPC177404
0.7248	Intermediate Similarity	NPC476131
0.7241	Intermediate Similarity	NPC329825
0.7229	Intermediate Similarity	NPC41717
0.7228	Intermediate Similarity	NPC309498
0.7215	Intermediate Similarity	NPC161292
0.7212	Intermediate Similarity	NPC311276
0.7204	Intermediate Similarity	NPC472752
0.7203	Intermediate Similarity	NPC143603
0.72	Intermediate Similarity	NPC69914
0.7191	Intermediate Similarity	NPC103230
0.7178	Intermediate Similarity	NPC129721
0.7176	Intermediate Similarity	NPC150048
0.7176	Intermediate Similarity	NPC203754
0.716	Intermediate Similarity	NPC63562
0.7143	Intermediate Similarity	NPC27740
0.7134	Intermediate Similarity	NPC113812
0.7126	Intermediate Similarity	NPC284678
0.7126	Intermediate Similarity	NPC207851
0.7108	Intermediate Similarity	NPC102423
0.7101	Intermediate Similarity	NPC14651
0.7101	Intermediate Similarity	NPC158129
0.7101	Intermediate Similarity	NPC121658
0.7095	Intermediate Similarity	NPC166424
0.7095	Intermediate Similarity	NPC245244
0.7095	Intermediate Similarity	NPC146373
0.7091	Intermediate Similarity	NPC324203
0.7091	Intermediate Similarity	NPC131718
0.7091	Intermediate Similarity	NPC322976
0.7091	Intermediate Similarity	NPC63338
0.7088	Intermediate Similarity	NPC123395
0.7081	Intermediate Similarity	NPC24678
0.7081	Intermediate Similarity	NPC105818
0.7081	Intermediate Similarity	NPC289086
0.7073	Intermediate Similarity	NPC469762
0.7073	Intermediate Similarity	NPC269919
0.7073	Intermediate Similarity	NPC132680
0.7063	Intermediate Similarity	NPC477974
0.7062	Intermediate Similarity	NPC44354
0.7059	Intermediate Similarity	NPC313791
0.7056	Intermediate Similarity	NPC135950
0.7052	Intermediate Similarity	NPC317010
0.7041	Intermediate Similarity	NPC476518
0.7039	Intermediate Similarity	NPC195268
0.7039	Intermediate Similarity	NPC133140
0.7037	Intermediate Similarity	NPC153769
0.7032	Intermediate Similarity	NPC65408
0.703	Intermediate Similarity	NPC84508
0.7021	Intermediate Similarity	NPC235843
0.7021	Intermediate Similarity	NPC472550
0.7021	Intermediate Similarity	NPC304179
0.7021	Intermediate Similarity	NPC48042
0.7012	Intermediate Similarity	NPC469785
0.7011	Intermediate Similarity	NPC219963
0.7006	Intermediate Similarity	NPC325775
0.7006	Intermediate Similarity	NPC328798
0.7	Intermediate Similarity	NPC307963
0.6995	Remote Similarity	NPC103361
0.6994	Remote Similarity	NPC469763
0.6994	Remote Similarity	NPC73952
0.6994	Remote Similarity	NPC469786
0.6994	Remote Similarity	NPC469760
0.6994	Remote Similarity	NPC469765
0.6994	Remote Similarity	NPC25008
0.6994	Remote Similarity	NPC259644
0.6989	Remote Similarity	NPC280290
0.6988	Remote Similarity	NPC25899
0.6977	Remote Similarity	NPC476419
0.6968	Remote Similarity	NPC63041
0.6963	Remote Similarity	NPC83987
0.6959	Remote Similarity	NPC46358
0.6957	Remote Similarity	NPC477019
0.6951	Remote Similarity	NPC211572
0.6951	Remote Similarity	NPC70922
0.6951	Remote Similarity	NPC80597
0.6951	Remote Similarity	NPC212376
0.6951	Remote Similarity	NPC75540
0.6943	Remote Similarity	NPC162812
0.694	Remote Similarity	NPC324245
0.694	Remote Similarity	NPC320748
0.6928	Remote Similarity	NPC174421
0.6928	Remote Similarity	NPC230869
0.6923	Remote Similarity	NPC314102
0.6923	Remote Similarity	NPC160105
0.6923	Remote Similarity	NPC251722
0.6923	Remote Similarity	NPC473053
0.6919	Remote Similarity	NPC32451
0.6919	Remote Similarity	NPC328559
0.6914	Remote Similarity	NPC266551
0.6914	Remote Similarity	NPC161887
0.6911	Remote Similarity	NPC292517
0.6911	Remote Similarity	NPC476467
0.6911	Remote Similarity	NPC472553
0.6906	Remote Similarity	NPC231655
0.6905	Remote Similarity	NPC476446
0.6905	Remote Similarity	NPC78375
0.6905	Remote Similarity	NPC211187
0.6905	Remote Similarity	NPC40779
0.6905	Remote Similarity	NPC469813
0.6901	Remote Similarity	NPC273532
0.6899	Remote Similarity	NPC318935
0.6894	Remote Similarity	NPC220523
0.6893	Remote Similarity	NPC62510
0.6893	Remote Similarity	NPC282103
0.689	Remote Similarity	NPC26872
0.6878	Remote Similarity	NPC470190
0.6875	Remote Similarity	NPC48938
0.6875	Remote Similarity	NPC327373
0.6865	Remote Similarity	NPC79223
0.6865	Remote Similarity	NPC470279
0.6863	Remote Similarity	NPC282398
0.686	Remote Similarity	NPC111624
0.686	Remote Similarity	NPC314603
0.6856	Remote Similarity	NPC477908
0.6856	Remote Similarity	NPC206343
0.6848	Remote Similarity	NPC239954
0.6848	Remote Similarity	NPC477815
0.6845	Remote Similarity	NPC48192
0.6842	Remote Similarity	NPC471589
0.6842	Remote Similarity	NPC256828
0.6839	Remote Similarity	NPC319128
0.6839	Remote Similarity	NPC228331
0.6839	Remote Similarity	NPC283152
0.6835	Remote Similarity	NPC32002
0.6835	Remote Similarity	NPC316811
0.6835	Remote Similarity	NPC315348
0.6833	Remote Similarity	NPC76748
0.6832	Remote Similarity	NPC159856
0.6832	Remote Similarity	NPC314372
0.6831	Remote Similarity	NPC251090
0.6824	Remote Similarity	NPC474561
0.6824	Remote Similarity	NPC49954
0.6818	Remote Similarity	NPC101165
0.6813	Remote Similarity	NPC198673
0.6813	Remote Similarity	NPC190296
0.6809	Remote Similarity	NPC165349
0.6809	Remote Similarity	NPC329708

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 NPC471323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	627
0.2-0.3	922
0.3-0.4	1188
0.4-0.5	3352
0.5-0.6	2217
0.6-0.7	571
0.7-0.8	99
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8613	High Similarity	NPD9284	Approved
0.8462	Intermediate Similarity	NPD9506	Approved
0.8367	Intermediate Similarity	NPD3813	Approved
0.8345	Intermediate Similarity	NPD9080	Approved
0.8288	Intermediate Similarity	NPD1649	Discontinued
0.8276	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1352	Discontinued
0.8086	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2581	Approved
0.8065	Intermediate Similarity	NPD820	Phase 3
0.8065	Intermediate Similarity	NPD2582	Approved
0.805	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD8063	Discontinued
0.7961	Intermediate Similarity	NPD9271	Approved
0.7927	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3717	Discontinued
0.7667	Intermediate Similarity	NPD2896	Discontinued
0.7632	Intermediate Similarity	NPD4805	Approved
0.763	Intermediate Similarity	NPD4376	Phase 3
0.7616	Intermediate Similarity	NPD6281	Approved
0.7613	Intermediate Similarity	NPD4703	Approved
0.7613	Intermediate Similarity	NPD4702	Approved
0.7597	Intermediate Similarity	NPD9075	Approved
0.7597	Intermediate Similarity	NPD9074	Approved
0.7576	Intermediate Similarity	NPD2076	Approved
0.7576	Intermediate Similarity	NPD2077	Approved
0.7566	Intermediate Similarity	NPD107	Approved
0.7562	Intermediate Similarity	NPD5255	Approved
0.7551	Intermediate Similarity	NPD9206	Approved
0.7551	Intermediate Similarity	NPD9207	Approved
0.7545	Intermediate Similarity	NPD4072	Approved
0.7545	Intermediate Similarity	NPD4071	Approved
0.7518	Intermediate Similarity	NPD4823	Approved
0.7518	Intermediate Similarity	NPD4824	Approved
0.7516	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2511	Approved
0.7515	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4804	Approved
0.7485	Intermediate Similarity	NPD5100	Phase 3
0.7457	Intermediate Similarity	NPD4021	Phase 2
0.7438	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7469	Discontinued
0.7423	Intermediate Similarity	NPD5088	Discontinued
0.7415	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD271	Approved
0.7413	Intermediate Similarity	NPD268	Approved
0.7413	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2809	Approved
0.7357	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2599	Approved
0.7353	Intermediate Similarity	NPD2601	Approved
0.7353	Intermediate Similarity	NPD2600	Approved
0.7347	Intermediate Similarity	NPD2118	Approved
0.7347	Intermediate Similarity	NPD2119	Approved
0.7321	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1380	Discovery
0.731	Intermediate Similarity	NPD3386	Phase 2
0.731	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5862	Discovery
0.7288	Intermediate Similarity	NPD4551	Phase 2
0.7288	Intermediate Similarity	NPD4529	Approved
0.7288	Intermediate Similarity	NPD4528	Approved
0.7288	Intermediate Similarity	NPD4526	Approved
0.7263	Intermediate Similarity	NPD2952	Discontinued
0.7256	Intermediate Similarity	NPD8026	Phase 1
0.725	Intermediate Similarity	NPD3262	Approved
0.7247	Intermediate Similarity	NPD3396	Approved
0.7247	Intermediate Similarity	NPD3395	Approved
0.7241	Intermediate Similarity	NPD4375	Approved
0.7238	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1032	Phase 2
0.7232	Intermediate Similarity	NPD6569	Phase 2
0.7222	Intermediate Similarity	NPD6026	Approved
0.7219	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6635	Approved
0.7202	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3476	Approved
0.72	Intermediate Similarity	NPD3475	Approved
0.7193	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3082	Discontinued
0.7179	Intermediate Similarity	NPD1382	Phase 2
0.7179	Intermediate Similarity	NPD1383	Phase 3
0.7169	Intermediate Similarity	NPD925	Approved
0.7169	Intermediate Similarity	NPD926	Approved
0.7162	Intermediate Similarity	NPD9583	Approved
0.716	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9726	Discontinued
0.7143	Intermediate Similarity	NPD2882	Phase 1
0.7143	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9357	Approved
0.7135	Intermediate Similarity	NPD8123	Approved
0.7135	Intermediate Similarity	NPD8122	Approved
0.7134	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1096	Discontinued
0.7126	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1993	Approved
0.7105	Intermediate Similarity	NPD1994	Approved
0.7105	Intermediate Similarity	NPD1995	Approved
0.7104	Intermediate Similarity	NPD3911	Approved
0.7102	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1418	Phase 2
0.7086	Intermediate Similarity	NPD4889	Approved
0.7081	Intermediate Similarity	NPD7396	Approved
0.7079	Intermediate Similarity	NPD4699	Discontinued
0.7073	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9383	Approved
0.7073	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9382	Approved
0.7073	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1661	Suspended
0.7063	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3942	Approved
0.7059	Intermediate Similarity	NPD4029	Approved
0.7059	Intermediate Similarity	NPD4030	Approved
0.7059	Intermediate Similarity	NPD4028	Approved
0.7059	Intermediate Similarity	NPD3944	Approved
0.7045	Intermediate Similarity	NPD7757	Approved
0.7045	Intermediate Similarity	NPD7758	Approved
0.7039	Intermediate Similarity	NPD3921	Approved
0.7039	Intermediate Similarity	NPD3922	Approved
0.7039	Intermediate Similarity	NPD3924	Approved
0.7039	Intermediate Similarity	NPD6665	Discontinued
0.7039	Intermediate Similarity	NPD3923	Approved
0.7037	Intermediate Similarity	NPD9595	Approved
0.7037	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9596	Approved
0.7032	Intermediate Similarity	NPD200	Phase 2
0.7032	Intermediate Similarity	NPD201	Phase 2
0.7024	Intermediate Similarity	NPD425	Approved
0.7024	Intermediate Similarity	NPD424	Approved
0.7022	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5065	Approved
0.7011	Intermediate Similarity	NPD4203	Approved
0.7011	Intermediate Similarity	NPD4204	Approved
0.7006	Intermediate Similarity	NPD1034	Phase 3
0.7006	Intermediate Similarity	NPD8021	Approved
0.7006	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8020	Approved
0.7	Intermediate Similarity	NPD6361	Phase 2
0.7	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD991	Phase 2
0.7	Intermediate Similarity	NPD1038	Approved
0.7	Intermediate Similarity	NPD1598	Discontinued
0.7	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2781	Approved
0.6978	Remote Similarity	NPD1622	Discontinued
0.6974	Remote Similarity	NPD715	Phase 3
0.6968	Remote Similarity	NPD792	Discontinued
0.6964	Remote Similarity	NPD2780	Approved
0.6964	Remote Similarity	NPD2782	Approved
0.6962	Remote Similarity	NPD5020	Approved
0.6959	Remote Similarity	NPD1599	Approved
0.6946	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4372	Phase 1
0.6941	Remote Similarity	NPD565	Phase 2
0.6941	Remote Similarity	NPD5319	Approved
0.6941	Remote Similarity	NPD5320	Approved
0.6936	Remote Similarity	NPD2144	Approved
0.6933	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6158	Phase 2
0.6932	Remote Similarity	NPD3569	Discontinued
0.6931	Remote Similarity	NPD6529	Discontinued
0.6928	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3321	Discontinued
0.6923	Remote Similarity	NPD5611	Phase 2
0.6923	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3525	Discontinued
0.6914	Remote Similarity	NPD3575	Approved
0.6914	Remote Similarity	NPD3576	Approved
0.6906	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9098	Phase 3
0.6903	Remote Similarity	NPD2142	Approved
0.6903	Remote Similarity	NPD2140	Approved
0.6903	Remote Similarity	NPD2141	Approved
0.6902	Remote Similarity	NPD5999	Phase 2
0.6899	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9392	Approved
0.6897	Remote Similarity	NPD9396	Approved
0.6893	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4638	Approved
0.6882	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4640	Approved
0.6882	Remote Similarity	NPD4639	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