NPASS Compound

Structure

CID69213 OpenBabel06191715402D 20 24 0 0 0 0 0 0 0 0999 V2000 1.5616 -3.6048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7811 -4.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5616 -2.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -3.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7808 -1.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3412 -1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6438 -3.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7810 -2.2529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -2.7036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5607 -0.9014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3410 -2.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7800 -1.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7798 -2.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5603 -2.7039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5609 -0.0003 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 -2.2185 0.6571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0106 -2.8568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7475 -3.5856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 2 0 0 0 0 4 9 2 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	263.06
Volume:	258.786
LogP:	4.395
LogD:	3.274
LogS:	-7.532
# Rotatable Bonds:	0
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.601
Fsp3:	0.062
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:	-4.924
MDCK Permeability:	1.901377981994301e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.603

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	95.76410675048828%
Volume Distribution (VD):	0.707
Pgp-substrate:	2.2336297035217285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.216
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.834
CYP2D6-substrate:	0.43
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	8.214
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.862
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.819
Skin Sensitization:	0.917
Carcinogencity:	0.937
Eye Corrosion:	0.008
Eye Irritation:	0.714
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC69213

Natural Product ID:	NPC69213
*Common Name:**	Aristolactam Ii
IUPAC Name:	n.a.
Synonyms:	Aristolactam II
Standard InCHIKey:	KPVDACWQNCRKTG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H9NO3/c18-16-10-6-12-15(20-7-19-12)14-9-4-2-1-3-8(9)5-11(17-16)13(10)14/h1-6H,7H2,(H,17,18)
SMILES:	c1ccc2c(c1)cc1c3c(cc4c(c23)OCO4)C(=N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL603073
PubChem CID:	148745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[12880323]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1431939]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20097074]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21353775]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	=	15000.0	nM	PMID[549824]

☑ 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 NPC69213 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	550
0.1-0.2	2331
0.2-0.3	9914
0.3-0.4	7653
0.4-0.5	7767
0.5-0.6	11733
0.6-0.7	2479
0.7-0.8	236
0.8-0.85	14
0.85-0.9	3
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC112676
0.9881	High Similarity	NPC296742
0.9821	High Similarity	NPC224293
0.9538	High Similarity	NPC29472
0.9521	High Similarity	NPC265383
0.9464	High Similarity	NPC260118
0.9408	High Similarity	NPC215747
0.9408	High Similarity	NPC192939
0.9353	High Similarity	NPC119579
0.9298	High Similarity	NPC28425
0.9294	High Similarity	NPC311936
0.9222	High Similarity	NPC159101
0.908	High Similarity	NPC219170
0.908	High Similarity	NPC180253
0.9075	High Similarity	NPC276060
0.892	High Similarity	NPC22928
0.8771	High Similarity	NPC294244
0.8251	Intermediate Similarity	NPC474904
0.8251	Intermediate Similarity	NPC312531
0.8232	Intermediate Similarity	NPC249405
0.8095	Intermediate Similarity	NPC16436
0.8041	Intermediate Similarity	NPC46679
0.8032	Intermediate Similarity	NPC162653
0.8	Intermediate Similarity	NPC85661
0.8	Intermediate Similarity	NPC121510
0.8	Intermediate Similarity	NPC77359
0.8	Intermediate Similarity	NPC171882
0.7903	Intermediate Similarity	NPC320088
0.7901	Intermediate Similarity	NPC228040
0.7892	Intermediate Similarity	NPC276674
0.7892	Intermediate Similarity	NPC33902
0.788	Intermediate Similarity	NPC179704
0.7869	Intermediate Similarity	NPC190461
0.7814	Intermediate Similarity	NPC287588
0.7802	Intermediate Similarity	NPC285941
0.7795	Intermediate Similarity	NPC38961
0.7789	Intermediate Similarity	NPC91234
0.7784	Intermediate Similarity	NPC235628
0.7772	Intermediate Similarity	NPC320223
0.7772	Intermediate Similarity	NPC114364
0.776	Intermediate Similarity	NPC477558
0.7759	Intermediate Similarity	NPC18614
0.7737	Intermediate Similarity	NPC78284
0.7737	Intermediate Similarity	NPC302001
0.7722	Intermediate Similarity	NPC219341
0.7711	Intermediate Similarity	NPC290227
0.7705	Intermediate Similarity	NPC474051
0.7704	Intermediate Similarity	NPC244606
0.7704	Intermediate Similarity	NPC156728
0.7701	Intermediate Similarity	NPC52475
0.768	Intermediate Similarity	NPC247389
0.768	Intermediate Similarity	NPC298979
0.7673	Intermediate Similarity	NPC240684
0.7667	Intermediate Similarity	NPC225774
0.7663	Intermediate Similarity	NPC199465
0.7663	Intermediate Similarity	NPC229166
0.7663	Intermediate Similarity	NPC128560
0.7647	Intermediate Similarity	NPC248642
0.7634	Intermediate Similarity	NPC126284
0.7624	Intermediate Similarity	NPC24264
0.7624	Intermediate Similarity	NPC476432
0.7624	Intermediate Similarity	NPC68328
0.7606	Intermediate Similarity	NPC156576
0.7606	Intermediate Similarity	NPC135772
0.7596	Intermediate Similarity	NPC152212
0.7582	Intermediate Similarity	NPC210918
0.7569	Intermediate Similarity	NPC302527
0.7569	Intermediate Similarity	NPC16805
0.7569	Intermediate Similarity	NPC167546
0.7562	Intermediate Similarity	NPC61731
0.7562	Intermediate Similarity	NPC186569
0.756	Intermediate Similarity	NPC254610
0.7556	Intermediate Similarity	NPC24954
0.7554	Intermediate Similarity	NPC168153
0.7554	Intermediate Similarity	NPC231371
0.7553	Intermediate Similarity	NPC476575
0.7551	Intermediate Similarity	NPC295676
0.7538	Intermediate Similarity	NPC212163
0.75	Intermediate Similarity	NPC266753
0.75	Intermediate Similarity	NPC160298
0.75	Intermediate Similarity	NPC232924
0.75	Intermediate Similarity	NPC155442
0.75	Intermediate Similarity	NPC477561
0.75	Intermediate Similarity	NPC477559
0.75	Intermediate Similarity	NPC312918
0.75	Intermediate Similarity	NPC306902
0.75	Intermediate Similarity	NPC476574
0.7488	Intermediate Similarity	NPC124658
0.7488	Intermediate Similarity	NPC227361
0.7486	Intermediate Similarity	NPC211296
0.7471	Intermediate Similarity	NPC77572
0.746	Intermediate Similarity	NPC116284
0.7452	Intermediate Similarity	NPC118121
0.7444	Intermediate Similarity	NPC69360
0.7435	Intermediate Similarity	NPC57036
0.7427	Intermediate Similarity	NPC204446
0.7418	Intermediate Similarity	NPC189470
0.7405	Intermediate Similarity	NPC6152
0.7398	Intermediate Similarity	NPC23080
0.7398	Intermediate Similarity	NPC193906
0.7394	Intermediate Similarity	NPC118633
0.7394	Intermediate Similarity	NPC294790
0.7394	Intermediate Similarity	NPC148693
0.7391	Intermediate Similarity	NPC474931
0.7391	Intermediate Similarity	NPC306555
0.7391	Intermediate Similarity	NPC81218
0.7391	Intermediate Similarity	NPC12053
0.7391	Intermediate Similarity	NPC145832
0.7391	Intermediate Similarity	NPC158376
0.7391	Intermediate Similarity	NPC117188
0.7391	Intermediate Similarity	NPC205421
0.7377	Intermediate Similarity	NPC168409
0.7366	Intermediate Similarity	NPC235076
0.7366	Intermediate Similarity	NPC149090
0.7366	Intermediate Similarity	NPC19520
0.7356	Intermediate Similarity	NPC145304
0.7353	Intermediate Similarity	NPC251160
0.7344	Intermediate Similarity	NPC214116
0.734	Intermediate Similarity	NPC188420
0.7337	Intermediate Similarity	NPC304659
0.7337	Intermediate Similarity	NPC86144
0.7327	Intermediate Similarity	NPC100573
0.7327	Intermediate Similarity	NPC90185
0.7327	Intermediate Similarity	NPC207873
0.7322	Intermediate Similarity	NPC1229
0.7318	Intermediate Similarity	NPC10875
0.7318	Intermediate Similarity	NPC10730
0.7316	Intermediate Similarity	NPC474506
0.7316	Intermediate Similarity	NPC32413
0.7308	Intermediate Similarity	NPC46451
0.7308	Intermediate Similarity	NPC256422
0.7306	Intermediate Similarity	NPC476576
0.7306	Intermediate Similarity	NPC186546
0.7302	Intermediate Similarity	NPC206201
0.7297	Intermediate Similarity	NPC304846
0.7293	Intermediate Similarity	NPC476572
0.7283	Intermediate Similarity	NPC13504
0.7283	Intermediate Similarity	NPC306843
0.7283	Intermediate Similarity	NPC54125
0.7283	Intermediate Similarity	NPC196447
0.7283	Intermediate Similarity	NPC253043
0.7283	Intermediate Similarity	NPC212794
0.7283	Intermediate Similarity	NPC78222
0.7283	Intermediate Similarity	NPC89199
0.7283	Intermediate Similarity	NPC136508
0.7283	Intermediate Similarity	NPC477563
0.7283	Intermediate Similarity	NPC96603
0.7277	Intermediate Similarity	NPC275132
0.7268	Intermediate Similarity	NPC82763
0.7264	Intermediate Similarity	NPC200888
0.7263	Intermediate Similarity	NPC267408
0.7263	Intermediate Similarity	NPC470879
0.7263	Intermediate Similarity	NPC258695
0.7263	Intermediate Similarity	NPC275027
0.726	Intermediate Similarity	NPC100079
0.726	Intermediate Similarity	NPC23614
0.7258	Intermediate Similarity	NPC241055
0.7258	Intermediate Similarity	NPC182257
0.7249	Intermediate Similarity	NPC112575
0.7236	Intermediate Similarity	NPC25897
0.7234	Intermediate Similarity	NPC192135
0.7234	Intermediate Similarity	NPC477020
0.7234	Intermediate Similarity	NPC66341
0.7233	Intermediate Similarity	NPC149471
0.7233	Intermediate Similarity	NPC271215
0.7228	Intermediate Similarity	NPC261388
0.7228	Intermediate Similarity	NPC324144
0.7225	Intermediate Similarity	NPC148409
0.7219	Intermediate Similarity	NPC474953
0.7213	Intermediate Similarity	NPC166014
0.7213	Intermediate Similarity	NPC27410
0.7211	Intermediate Similarity	NPC23219
0.7206	Intermediate Similarity	NPC168250
0.7198	Intermediate Similarity	NPC55470
0.7194	Intermediate Similarity	NPC117717
0.7182	Intermediate Similarity	NPC99659
0.7182	Intermediate Similarity	NPC76079
0.7182	Intermediate Similarity	NPC325871
0.7174	Intermediate Similarity	NPC60186
0.715	Intermediate Similarity	NPC204385
0.715	Intermediate Similarity	NPC234197
0.7143	Intermediate Similarity	NPC475754
0.7143	Intermediate Similarity	NPC110374
0.7143	Intermediate Similarity	NPC289743
0.7143	Intermediate Similarity	NPC2314
0.7143	Intermediate Similarity	NPC79213
0.7136	Intermediate Similarity	NPC17677
0.7135	Intermediate Similarity	NPC19555
0.7128	Intermediate Similarity	NPC118274
0.7128	Intermediate Similarity	NPC69712
0.7128	Intermediate Similarity	NPC26240
0.7128	Intermediate Similarity	NPC477562
0.7128	Intermediate Similarity	NPC168753
0.7126	Intermediate Similarity	NPC470090
0.7112	Intermediate Similarity	NPC310894
0.7112	Intermediate Similarity	NPC150879
0.7111	Intermediate Similarity	NPC326316
0.7111	Intermediate Similarity	NPC81733
0.7105	Intermediate Similarity	NPC187678
0.7104	Intermediate Similarity	NPC210296

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 NPC69213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	792
0.2-0.3	964
0.3-0.4	2105
0.4-0.5	2690
0.5-0.6	1864
0.6-0.7	362
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7684	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5617	Suspended
0.7312	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3763	Approved
0.7247	Intermediate Similarity	NPD2883	Discontinued
0.7207	Intermediate Similarity	NPD5811	Approved
0.7165	Intermediate Similarity	NPD3349	Phase 2
0.7135	Intermediate Similarity	NPD1850	Phase 3
0.7128	Intermediate Similarity	NPD2843	Phase 2
0.7128	Intermediate Similarity	NPD2845	Phase 2
0.7112	Intermediate Similarity	NPD4083	Discontinued
0.7033	Intermediate Similarity	NPD3778	Approved
0.7027	Intermediate Similarity	NPD5604	Discontinued
0.7016	Intermediate Similarity	NPD3920	Phase 2
0.7006	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3296	Phase 1
0.6961	Remote Similarity	NPD950	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5582	Discontinued
0.6935	Remote Similarity	NPD3453	Discontinued
0.6904	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6184	Discontinued
0.6878	Remote Similarity	NPD3051	Approved
0.6872	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3816	Phase 1
0.6857	Remote Similarity	NPD3815	Phase 1
0.6848	Remote Similarity	NPD2789	Approved
0.6845	Remote Similarity	NPD4055	Discovery
0.6842	Remote Similarity	NPD2969	Approved
0.6842	Remote Similarity	NPD2970	Approved
0.6834	Remote Similarity	NPD5641	Discontinued
0.6831	Remote Similarity	NPD4005	Discontinued
0.6827	Remote Similarity	NPD4859	Phase 1
0.6825	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2821	Approved
0.6818	Remote Similarity	NPD8067	Phase 3
0.6804	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4123	Phase 3
0.6789	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5810	Discontinued
0.6776	Remote Similarity	NPD4003	Phase 3
0.6771	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3236	Phase 3
0.6757	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7479	Phase 2
0.6748	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5599	Discontinued
0.6737	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2489	Approved
0.6719	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD27	Approved
0.671	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4577	Approved
0.6701	Remote Similarity	NPD4578	Approved
0.6685	Remote Similarity	NPD1375	Discontinued
0.6683	Remote Similarity	NPD4951	Discontinued
0.6683	Remote Similarity	NPD7262	Phase 1
0.6682	Remote Similarity	NPD6723	Discontinued
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7034	Discontinued
0.6667	Remote Similarity	NPD6331	Phase 2
0.6667	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2674	Phase 3
0.6651	Remote Similarity	NPD5530	Phase 1
0.665	Remote Similarity	NPD7906	Approved
0.665	Remote Similarity	NPD3398	Discontinued
0.665	Remote Similarity	NPD5800	Discontinued
0.6648	Remote Similarity	NPD4097	Suspended
0.6634	Remote Similarity	NPD3924	Approved
0.6634	Remote Similarity	NPD3922	Approved
0.6634	Remote Similarity	NPD3963	Phase 1
0.6634	Remote Similarity	NPD3921	Approved
0.6634	Remote Similarity	NPD3923	Approved
0.663	Remote Similarity	NPD3301	Approved
0.663	Remote Similarity	NPD5241	Discontinued
0.6629	Remote Similarity	NPD2161	Phase 2
0.662	Remote Similarity	NPD7827	Phase 1
0.6616	Remote Similarity	NPD7546	Discontinued
0.6613	Remote Similarity	NPD4678	Approved
0.6613	Remote Similarity	NPD4675	Approved
0.6607	Remote Similarity	NPD6494	Phase 2
0.6601	Remote Similarity	NPD7125	Discontinued
0.66	Remote Similarity	NPD4663	Approved
0.6597	Remote Similarity	NPD6037	Discontinued
0.6578	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4108	Discontinued
0.657	Remote Similarity	NPD6612	Phase 2
0.6564	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3983	Phase 3
0.6562	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2560	Approved
0.6561	Remote Similarity	NPD2563	Approved
0.6557	Remote Similarity	NPD2420	Approved
0.6557	Remote Similarity	NPD2421	Approved
0.6556	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4481	Phase 3
0.6537	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7312	Approved
0.6533	Remote Similarity	NPD7311	Approved
0.6533	Remote Similarity	NPD7310	Approved
0.6533	Remote Similarity	NPD7313	Approved
0.6522	Remote Similarity	NPD4584	Approved
0.6514	Remote Similarity	NPD3145	Approved
0.6514	Remote Similarity	NPD3144	Approved
0.6508	Remote Similarity	NPD2977	Approved
0.6508	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD2978	Approved
0.6507	Remote Similarity	NPD3515	Approved
0.6507	Remote Similarity	NPD3516	Approved
0.6505	Remote Similarity	NPD6527	Approved
0.6503	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7309	Approved
0.6498	Remote Similarity	NPD5164	Discontinued
0.6492	Remote Similarity	NPD7831	Phase 2
0.6492	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7833	Phase 2
0.6491	Remote Similarity	NPD1669	Approved
0.6488	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6340	Approved
0.6468	Remote Similarity	NPD6339	Approved
0.6467	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4357	Discontinued
0.6465	Remote Similarity	NPD7007	Discovery
0.6462	Remote Similarity	NPD7263	Phase 2
0.6462	Remote Similarity	NPD5429	Discontinued
0.6455	Remote Similarity	NPD37	Approved
0.6453	Remote Similarity	NPD3342	Phase 2
0.6446	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6071	Discontinued
0.6442	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.644	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.644	Remote Similarity	NPD4967	Phase 2
0.644	Remote Similarity	NPD4965	Approved
0.644	Remote Similarity	NPD4966	Approved
0.6432	Remote Similarity	NPD5658	Approved
0.6429	Remote Similarity	NPD6674	Discontinued
0.6421	Remote Similarity	NPD5929	Approved
0.6419	Remote Similarity	NPD4502	Phase 2
0.6418	Remote Similarity	NPD8053	Approved
0.6418	Remote Similarity	NPD8054	Approved
0.6411	Remote Similarity	NPD3289	Phase 3
0.6411	Remote Similarity	NPD3290	Approved
0.6408	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4319	Phase 2
0.6396	Remote Similarity	NPD3909	Discontinued
0.6394	Remote Similarity	NPD6877	Discontinued
0.6393	Remote Similarity	NPD5819	Phase 2
0.6385	Remote Similarity	NPD7222	Phase 2
0.6385	Remote Similarity	NPD7453	Approved
0.6385	Remote Similarity	NPD7452	Approved
0.6384	Remote Similarity	NPD7477	Discontinued
0.6378	Remote Similarity	NPD2898	Approved
0.6376	Remote Similarity	NPD5805	Approved
0.6376	Remote Similarity	NPD8149	Discontinued
0.6374	Remote Similarity	NPD3705	Approved
0.6373	Remote Similarity	NPD4796	Discontinued
0.6373	Remote Similarity	NPD6234	Discontinued
0.6369	Remote Similarity	NPD2157	Approved
0.6368	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6030	Approved
0.6364	Remote Similarity	NPD6031	Approved
0.6359	Remote Similarity	NPD4356	Discontinued
0.6359	Remote Similarity	NPD6526	Approved
0.6354	Remote Similarity	NPD1742	Approved
0.6354	Remote Similarity	NPD19	Approved
0.6354	Remote Similarity	NPD7773	Phase 2
0.6354	Remote Similarity	NPD1743	Approved
0.6349	Remote Similarity	NPD6502	Phase 2
0.6346	Remote Similarity	NPD4604	Approved
0.6346	Remote Similarity	NPD4605	Approved
0.6344	Remote Similarity	NPD7020	Approved
0.6344	Remote Similarity	NPD7019	Approved
0.6341	Remote Similarity	NPD2488	Approved
0.6341	Remote Similarity	NPD2490	Approved
0.634	Remote Similarity	NPD6746	Phase 2
0.6338	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5930	Phase 3
0.6335	Remote Similarity	NPD5773	Approved
0.6335	Remote Similarity	NPD5772	Approved
0.6332	Remote Similarity	NPD5557	Phase 1
0.6328	Remote Similarity	NPD5109	Approved
0.6328	Remote Similarity	NPD2322	Discovery
0.6328	Remote Similarity	NPD5110	Phase 2
0.6328	Remote Similarity	NPD5111	Phase 2
0.6327	Remote Similarity	NPD2215	Approved
0.6327	Remote Similarity	NPD7567	Approved
0.6327	Remote Similarity	NPD2216	Approved
0.6324	Remote Similarity	NPD1898	Discontinued
0.6324	Remote Similarity	NPD1305	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