NPASS Compound

Structure

NPC211997 OpenBabel07101719252D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.3371 3.3680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 -3.6646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0606 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2661 -3.0768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 1.2983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 2.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1250 2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 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 1.6126 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 2.9098 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 0.5387 4.1254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1615 -2.0823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 17 2 0 0 0 0 9 19 2 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 20 23 2 3 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	378.598
LogP:	3.519
LogD:	2.795
LogS:	-4.843
# Rotatable Bonds:	4
TPSA:	43.26
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	3.823
Fsp3:	0.5
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:	-4.689
MDCK Permeability:	2.3608004994457588e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	93.28792572021484%
Volume Distribution (VD):	1.032
Pgp-substrate:	4.563864707946777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.525
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.799
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.631
CYP2D6-substrate:	0.687
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	4.111
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.423
AMES Toxicity:	0.846
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.782
Skin Sensitization:	0.058
Carcinogencity:	0.607
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.16

Download Data

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

Natural Product: NPC211997

Natural Product ID:	NPC211997
*Common Name:**	UNVXNWJNODKIRV-JOCHJYFZSA-N
IUPAC Name:	n.a.
Synonyms:	5-Ethoxymethylrhazinilam
Standard InCHIKey:	UNVXNWJNODKIRV-JOCHJYFZSA-N
Standard InCHI:	InChI=1S/C22H28N2O2/c1-3-22-11-7-13-24-16(15-26-4-2)14-18(21(22)24)17-8-5-6-9-19(17)23-20(25)10-12-22/h5-6,8-9,14H,3-4,7,10-13,15H2,1-2H3,(H,23,25)/t22-/m1/s1
SMILES:	CC[C@@]12CCCn3c(cc(-c4ccccc4N=C(CC1)O)c23)COCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564900
PubChem CID:	25227569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles

*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
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665953]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	Yunnan, China	n.a.	PMID[19133778]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31241923]
NPO2700	Kopsia arborea	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7440.0	nM	PMID[473724]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6390.0	nM	PMID[473724]

☑ 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 NPC211997 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	324
0.1-0.2	1735
0.2-0.3	11999
0.3-0.4	15573
0.4-0.5	7243
0.5-0.6	3345
0.6-0.7	2116
0.7-0.8	353
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC134586
0.95	High Similarity	NPC158129
0.8476	Intermediate Similarity	NPC129721
0.8114	Intermediate Similarity	NPC133261
0.8047	Intermediate Similarity	NPC81229
0.8047	Intermediate Similarity	NPC255229
0.8	Intermediate Similarity	NPC472122
0.8	Intermediate Similarity	NPC24594
0.7978	Intermediate Similarity	NPC159125
0.795	Intermediate Similarity	NPC104483
0.791	Intermediate Similarity	NPC248462
0.7889	Intermediate Similarity	NPC62510
0.787	Intermediate Similarity	NPC141353
0.787	Intermediate Similarity	NPC285469
0.7865	Intermediate Similarity	NPC472105
0.7865	Intermediate Similarity	NPC187827
0.7853	Intermediate Similarity	NPC326575
0.7833	Intermediate Similarity	NPC284678
0.7801	Intermediate Similarity	NPC472111
0.7797	Intermediate Similarity	NPC56618
0.7784	Intermediate Similarity	NPC473178
0.7778	Intermediate Similarity	NPC472109
0.7778	Intermediate Similarity	NPC472110
0.7772	Intermediate Similarity	NPC469589
0.7714	Intermediate Similarity	NPC317430
0.7713	Intermediate Similarity	NPC239954
0.7709	Intermediate Similarity	NPC472443
0.7708	Intermediate Similarity	NPC475841
0.7708	Intermediate Similarity	NPC474145
0.7706	Intermediate Similarity	NPC207726
0.7697	Intermediate Similarity	NPC150048
0.7697	Intermediate Similarity	NPC203754
0.7696	Intermediate Similarity	NPC475774
0.7688	Intermediate Similarity	NPC16667
0.7688	Intermediate Similarity	NPC198673
0.7684	Intermediate Similarity	NPC34508
0.768	Intermediate Similarity	NPC472444
0.768	Intermediate Similarity	NPC19679
0.7667	Intermediate Similarity	NPC15840
0.7654	Intermediate Similarity	NPC64436
0.7634	Intermediate Similarity	NPC55493
0.7624	Intermediate Similarity	NPC314394
0.7624	Intermediate Similarity	NPC233936
0.7619	Intermediate Similarity	NPC168911
0.7609	Intermediate Similarity	NPC204565
0.76	Intermediate Similarity	NPC470508
0.7598	Intermediate Similarity	NPC121903
0.7584	Intermediate Similarity	NPC471294
0.7584	Intermediate Similarity	NPC472123
0.7582	Intermediate Similarity	NPC139291
0.7582	Intermediate Similarity	NPC48938
0.7582	Intermediate Similarity	NPC472108
0.7579	Intermediate Similarity	NPC241024
0.7579	Intermediate Similarity	NPC32200
0.7572	Intermediate Similarity	NPC67056
0.7568	Intermediate Similarity	NPC173028
0.7568	Intermediate Similarity	NPC65215
0.7556	Intermediate Similarity	NPC283152
0.7553	Intermediate Similarity	NPC133366
0.7542	Intermediate Similarity	NPC472586
0.7527	Intermediate Similarity	NPC113626
0.7526	Intermediate Similarity	NPC212213
0.7514	Intermediate Similarity	NPC317030
0.7514	Intermediate Similarity	NPC270009
0.75	Intermediate Similarity	NPC470507
0.75	Intermediate Similarity	NPC473189
0.75	Intermediate Similarity	NPC474177
0.7486	Intermediate Similarity	NPC143533
0.7486	Intermediate Similarity	NPC472104
0.7472	Intermediate Similarity	NPC280548
0.7471	Intermediate Similarity	NPC37548
0.746	Intermediate Similarity	NPC57994
0.746	Intermediate Similarity	NPC289299
0.7459	Intermediate Similarity	NPC293472
0.7459	Intermediate Similarity	NPC474707
0.7459	Intermediate Similarity	NPC234987
0.7458	Intermediate Similarity	NPC49954
0.7458	Intermediate Similarity	NPC474561
0.7449	Intermediate Similarity	NPC475910
0.7448	Intermediate Similarity	NPC214428
0.7446	Intermediate Similarity	NPC472119
0.7444	Intermediate Similarity	NPC329688
0.7444	Intermediate Similarity	NPC189812
0.7443	Intermediate Similarity	NPC469541
0.7443	Intermediate Similarity	NPC311276
0.7437	Intermediate Similarity	NPC469592
0.7437	Intermediate Similarity	NPC471080
0.7432	Intermediate Similarity	NPC192270
0.7421	Intermediate Similarity	NPC245916
0.7419	Intermediate Similarity	NPC472323
0.7419	Intermediate Similarity	NPC473177
0.7405	Intermediate Similarity	NPC79062
0.7405	Intermediate Similarity	NPC472107
0.7403	Intermediate Similarity	NPC84347
0.7399	Intermediate Similarity	NPC471458
0.7398	Intermediate Similarity	NPC53344
0.7389	Intermediate Similarity	NPC132642
0.7386	Intermediate Similarity	NPC282231
0.738	Intermediate Similarity	NPC46413
0.7371	Intermediate Similarity	NPC230869
0.7371	Intermediate Similarity	NPC57398
0.7368	Intermediate Similarity	NPC187951
0.7366	Intermediate Similarity	NPC66210
0.736	Intermediate Similarity	NPC54988
0.736	Intermediate Similarity	NPC160105
0.7358	Intermediate Similarity	NPC249040
0.7351	Intermediate Similarity	NPC320394
0.7351	Intermediate Similarity	NPC258480
0.7351	Intermediate Similarity	NPC284559
0.7347	Intermediate Similarity	NPC277350
0.7345	Intermediate Similarity	NPC476118
0.7345	Intermediate Similarity	NPC194640
0.7345	Intermediate Similarity	NPC118511
0.7345	Intermediate Similarity	NPC102423
0.7341	Intermediate Similarity	NPC26872
0.734	Intermediate Similarity	NPC95783
0.734	Intermediate Similarity	NPC469470
0.734	Intermediate Similarity	NPC469501
0.7337	Intermediate Similarity	NPC471323
0.7337	Intermediate Similarity	NPC242556
0.733	Intermediate Similarity	NPC131718
0.733	Intermediate Similarity	NPC279918
0.733	Intermediate Similarity	NPC251090
0.7321	Intermediate Similarity	NPC60553
0.7318	Intermediate Similarity	NPC201700
0.7318	Intermediate Similarity	NPC44161
0.7318	Intermediate Similarity	NPC63751
0.7316	Intermediate Similarity	NPC307963
0.7316	Intermediate Similarity	NPC79293
0.7316	Intermediate Similarity	NPC279401
0.7314	Intermediate Similarity	NPC469762
0.7312	Intermediate Similarity	NPC42591
0.7306	Intermediate Similarity	NPC128823
0.73	Intermediate Similarity	NPC472098
0.73	Intermediate Similarity	NPC264176
0.73	Intermediate Similarity	NPC118940
0.73	Intermediate Similarity	NPC94157
0.7299	Intermediate Similarity	NPC38736
0.7297	Intermediate Similarity	NPC176127
0.7296	Intermediate Similarity	NPC264166
0.7296	Intermediate Similarity	NPC274291
0.7296	Intermediate Similarity	NPC165349
0.7296	Intermediate Similarity	NPC118832
0.7296	Intermediate Similarity	NPC47059
0.7296	Intermediate Similarity	NPC329708
0.7293	Intermediate Similarity	NPC313791
0.7292	Intermediate Similarity	NPC267928
0.7292	Intermediate Similarity	NPC229332
0.7291	Intermediate Similarity	NPC469594
0.7288	Intermediate Similarity	NPC177404
0.7283	Intermediate Similarity	NPC469896
0.7278	Intermediate Similarity	NPC20144
0.7273	Intermediate Similarity	NPC478077
0.7268	Intermediate Similarity	NPC329747
0.7268	Intermediate Similarity	NPC329793
0.7262	Intermediate Similarity	NPC2949
0.7258	Intermediate Similarity	NPC84478
0.7257	Intermediate Similarity	NPC469785
0.7245	Intermediate Similarity	NPC476138
0.7245	Intermediate Similarity	NPC245816
0.7241	Intermediate Similarity	NPC73952
0.7241	Intermediate Similarity	NPC312645
0.7241	Intermediate Similarity	NPC469760
0.7241	Intermediate Similarity	NPC259644
0.7241	Intermediate Similarity	NPC25008
0.7241	Intermediate Similarity	NPC469763
0.7241	Intermediate Similarity	NPC469786
0.7241	Intermediate Similarity	NPC469765
0.7232	Intermediate Similarity	NPC473320
0.7228	Intermediate Similarity	NPC72980
0.7228	Intermediate Similarity	NPC219336
0.7219	Intermediate Similarity	NPC163421
0.7219	Intermediate Similarity	NPC188387
0.7216	Intermediate Similarity	NPC26850
0.7213	Intermediate Similarity	NPC288943
0.7211	Intermediate Similarity	NPC92111
0.7211	Intermediate Similarity	NPC472097
0.7211	Intermediate Similarity	NPC117244
0.7211	Intermediate Similarity	NPC473763
0.7204	Intermediate Similarity	NPC163055
0.72	Intermediate Similarity	NPC70922
0.72	Intermediate Similarity	NPC75540
0.72	Intermediate Similarity	NPC5145
0.72	Intermediate Similarity	NPC212376
0.72	Intermediate Similarity	NPC211572
0.72	Intermediate Similarity	NPC80597
0.7198	Intermediate Similarity	NPC314603
0.7196	Intermediate Similarity	NPC111602
0.7196	Intermediate Similarity	NPC196251
0.7196	Intermediate Similarity	NPC63199
0.7196	Intermediate Similarity	NPC102338
0.7196	Intermediate Similarity	NPC175474
0.7189	Intermediate Similarity	NPC478032
0.7184	Intermediate Similarity	NPC153769
0.7181	Intermediate Similarity	NPC171171
0.7181	Intermediate Similarity	NPC194040
0.7175	Intermediate Similarity	NPC84508
0.7174	Intermediate Similarity	NPC14325
0.7174	Intermediate Similarity	NPC28848
0.7174	Intermediate Similarity	NPC15573

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 NPC211997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	548
0.2-0.3	836
0.3-0.4	1053
0.4-0.5	2441
0.5-0.6	2939
0.6-0.7	1005
0.7-0.8	132
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8253	Intermediate Similarity	NPD2581	Approved
0.8253	Intermediate Similarity	NPD2582	Approved
0.8042	Intermediate Similarity	NPD7222	Phase 2
0.8023	Intermediate Similarity	NPD4204	Approved
0.8023	Intermediate Similarity	NPD4203	Approved
0.7967	Intermediate Similarity	NPD5913	Phase 3
0.7967	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2383	Phase 1
0.7865	Intermediate Similarity	NPD6452	Discontinued
0.7857	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7452	Approved
0.7853	Intermediate Similarity	NPD7453	Approved
0.7824	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD6281	Approved
0.7798	Intermediate Similarity	NPD6158	Phase 2
0.7798	Intermediate Similarity	NPD2882	Phase 1
0.7798	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD6227	Discontinued
0.7778	Intermediate Similarity	NPD5596	Phase 2
0.7754	Intermediate Similarity	NPD5003	Discontinued
0.7717	Intermediate Similarity	NPD2564	Approved
0.7717	Intermediate Similarity	NPD2565	Phase 2
0.7701	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5104	Approved
0.7692	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD2076	Approved
0.7684	Intermediate Similarity	NPD2077	Approved
0.7674	Intermediate Similarity	NPD5255	Approved
0.767	Intermediate Similarity	NPD1326	Approved
0.767	Intermediate Similarity	NPD1325	Approved
0.7637	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD8063	Discontinued
0.7614	Intermediate Similarity	NPD5862	Discovery
0.76	Intermediate Similarity	NPD2915	Discontinued
0.7598	Intermediate Similarity	NPD5100	Phase 3
0.759	Intermediate Similarity	NPD3525	Discontinued
0.7554	Intermediate Similarity	NPD5256	Discontinued
0.7551	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5065	Approved
0.754	Intermediate Similarity	NPD6569	Phase 2
0.7526	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4703	Approved
0.7515	Intermediate Similarity	NPD4702	Approved
0.75	Intermediate Similarity	NPD2381	Approved
0.75	Intermediate Similarity	NPD2380	Approved
0.75	Intermediate Similarity	NPD2382	Approved
0.75	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6590	Discontinued
0.746	Intermediate Similarity	NPD4602	Approved
0.746	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4418	Discontinued
0.7459	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6159	Phase 2
0.7436	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3385	Approved
0.7419	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4326	Phase 2
0.7411	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5075	Discontinued
0.7347	Intermediate Similarity	NPD3003	Approved
0.7347	Intermediate Similarity	NPD7001	Phase 3
0.7345	Intermediate Similarity	NPD5138	Approved
0.7345	Intermediate Similarity	NPD5140	Approved
0.7337	Intermediate Similarity	NPD7470	Discontinued
0.7337	Intermediate Similarity	NPD6220	Phase 3
0.7333	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2920	Discontinued
0.733	Intermediate Similarity	NPD5512	Phase 3
0.7326	Intermediate Similarity	NPD1034	Phase 3
0.7326	Intermediate Similarity	NPD3390	Phase 2
0.7326	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4640	Approved
0.7318	Intermediate Similarity	NPD4639	Approved
0.7318	Intermediate Similarity	NPD4638	Approved
0.7316	Intermediate Similarity	NPD4528	Approved
0.7316	Intermediate Similarity	NPD4526	Approved
0.7316	Intermediate Similarity	NPD4529	Approved
0.7316	Intermediate Similarity	NPD1038	Approved
0.7306	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4033	Approved
0.7296	Intermediate Similarity	NPD4036	Approved
0.7296	Intermediate Similarity	NPD31	Approved
0.7296	Intermediate Similarity	NPD4122	Approved
0.7296	Intermediate Similarity	NPD4037	Approved
0.7296	Intermediate Similarity	NPD4034	Approved
0.7296	Intermediate Similarity	NPD4039	Approved
0.7296	Intermediate Similarity	NPD4038	Approved
0.7296	Intermediate Similarity	NPD4035	Approved
0.7296	Intermediate Similarity	NPD32	Approved
0.7284	Intermediate Similarity	NPD3654	Approved
0.7278	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6492	Phase 2
0.724	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3477	Phase 2
0.7238	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3813	Approved
0.7234	Intermediate Similarity	NPD4948	Discontinued
0.7232	Intermediate Similarity	NPD1741	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5021	Discontinued
0.7219	Intermediate Similarity	NPD5020	Approved
0.7216	Intermediate Similarity	NPD1768	Approved
0.7216	Intermediate Similarity	NPD2175	Phase 3
0.7216	Intermediate Similarity	NPD2176	Approved
0.7216	Intermediate Similarity	NPD2177	Approved
0.7202	Intermediate Similarity	NPD1229	Phase 2
0.7198	Intermediate Similarity	NPD750	Phase 2
0.7198	Intermediate Similarity	NPD7418	Discontinued
0.7196	Intermediate Similarity	NPD4334	Discontinued
0.7189	Intermediate Similarity	NPD6595	Phase 3
0.7188	Intermediate Similarity	NPD6251	Discontinued
0.7182	Intermediate Similarity	NPD7474	Suspended
0.7174	Intermediate Similarity	NPD2144	Approved
0.7165	Intermediate Similarity	NPD53	Approved
0.7165	Intermediate Similarity	NPD7778	Approved
0.7165	Intermediate Similarity	NPD7777	Approved
0.7158	Intermediate Similarity	NPD4499	Approved
0.7157	Intermediate Similarity	NPD6991	Approved
0.715	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7935	Phase 2
0.7143	Intermediate Similarity	NPD5903	Approved
0.7143	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5902	Approved
0.7143	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8386	Phase 2
0.7135	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3330	Phase 1
0.7128	Intermediate Similarity	NPD6999	Discontinued
0.7128	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4463	Approved
0.7126	Intermediate Similarity	NPD4462	Approved
0.7118	Intermediate Similarity	NPD1592	Phase 3
0.7111	Intermediate Similarity	NPD926	Approved
0.7111	Intermediate Similarity	NPD925	Approved
0.7111	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5612	Discontinued
0.7107	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5658	Approved
0.7098	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5897	Approved
0.7097	Intermediate Similarity	NPD5898	Approved
0.7097	Intermediate Similarity	NPD5899	Approved
0.7087	Intermediate Similarity	NPD6455	Phase 3
0.7085	Intermediate Similarity	NPD5530	Phase 1
0.7083	Intermediate Similarity	NPD3404	Approved
0.7081	Intermediate Similarity	NPD1032	Phase 2
0.7081	Intermediate Similarity	NPD8122	Approved
0.7081	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6641	Approved
0.7081	Intermediate Similarity	NPD6642	Approved
0.7081	Intermediate Similarity	NPD8123	Approved
0.7079	Intermediate Similarity	NPD4502	Phase 2
0.7076	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3717	Discontinued
0.7068	Intermediate Similarity	NPD3321	Discontinued
0.7067	Intermediate Similarity	NPD6995	Phase 1
0.7062	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6550	Discontinued
0.7059	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3038	Discontinued
0.7059	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1392	Approved
0.7047	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3920	Phase 2
0.7039	Intermediate Similarity	NPD112	Approved
0.7039	Intermediate Similarity	NPD9705	Discontinued
0.7037	Intermediate Similarity	NPD3082	Discontinued
0.7035	Intermediate Similarity	NPD3397	Phase 2
0.7033	Intermediate Similarity	NPD2844	Phase 3
0.7031	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4699	Discontinued
0.7026	Intermediate Similarity	NPD6988	Phase 1
0.7026	Intermediate Similarity	NPD7948	Phase 1
0.7015	Intermediate Similarity	NPD2510	Approved
0.7015	Intermediate Similarity	NPD7672	Approved
0.7015	Intermediate Similarity	NPD7671	Approved
0.7015	Intermediate Similarity	NPD2509	Approved
0.7014	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6978	Phase 2
0.701	Intermediate Similarity	NPD7944	Discontinued
0.701	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3395	Approved
0.701	Intermediate Similarity	NPD3396	Approved
0.7006	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7194	Discontinued
0.7005	Intermediate Similarity	NPD3875	Discontinued

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