NPASS Compound

Structure

NPC159101 OpenBabel07101718222D 32 37 0 0 1 0 0 0 0 0999 V2000 -3.3023 -1.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 -1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1811 0.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2890 1.0903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0812 -1.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3023 -0.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3477 1.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7341 1.3067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4676 0.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5848 0.7810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7634 -0.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7048 -0.5403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9684 2.3529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9712 2.2782 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4941 3.2036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3183 -0.4193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0840 -1.4656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 2 0 0 0 0 1 3 1 0 0 0 0 2 8 1 0 0 0 0 3 12 2 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 24 1 0 0 0 0 7 29 1 0 0 0 0 7 30 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 31 1 0 0 0 0 13 20 2 0 0 0 0 13 29 1 0 0 0 0 14 6 1 6 0 0 0 14 17 1 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 22 1 0 0 0 0 19 27 1 1 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 22 31 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.11
Volume:	406.747
LogP:	1.666
LogD:	1.641
LogS:	-6.049
# Rotatable Bonds:	3
TPSA:	146.94
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	4.157
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-6.081
MDCK Permeability:	1.4653817743237596e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	89.7402572631836%
Volume Distribution (VD):	0.999
Pgp-substrate:	6.508467197418213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.226
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.84
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.849
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.673
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.071

Download Data

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

Natural Product: NPC159101

Natural Product ID:	NPC159101
*Common Name:**	BMZVZDXTSLWMHR-MAEOEUOPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BMZVZDXTSLWMHR-MAEOEUOPSA-N
Standard InCHI:	InChI=1S/C22H19NO9/c24-6-14-17(25)18(26)19(27)22(32-14)31-12-3-1-2-8-9(12)4-11-15-10(21(28)23-11)5-13-20(16(8)15)30-7-29-13/h1-5,14,17-19,22,24-27H,6-7H2,(H,23,28)/t14-,17-,18+,19-,22-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cccc3c2cc2N=C(c4c2c3c2OCOc2c4)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL601640
PubChem CID:	46232738
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]
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]
NPO18443	Aristolochia manshuriensis	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]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	>	10000.0	nM	PMID[534510]

☑ 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 NPC159101 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	493
0.1-0.2	1892
0.2-0.3	7161
0.3-0.4	10091
0.4-0.5	7603
0.5-0.6	11043
0.6-0.7	4137
0.7-0.8	256
0.8-0.85	9
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9227	High Similarity	NPC112676
0.9227	High Similarity	NPC296742
0.9222	High Similarity	NPC69213
0.9171	High Similarity	NPC224293
0.9027	High Similarity	NPC29472
0.884	High Similarity	NPC260118
0.8798	High Similarity	NPC28425
0.8791	High Similarity	NPC192939
0.8791	High Similarity	NPC215747
0.8785	High Similarity	NPC265383
0.8743	High Similarity	NPC119579
0.8689	High Similarity	NPC311936
0.8602	High Similarity	NPC219170
0.8602	High Similarity	NPC180253
0.8595	High Similarity	NPC276060
0.8556	High Similarity	NPC22928
0.8421	Intermediate Similarity	NPC294244
0.8031	Intermediate Similarity	NPC312531
0.801	Intermediate Similarity	NPC162653
0.7938	Intermediate Similarity	NPC474904
0.7824	Intermediate Similarity	NPC249405
0.7817	Intermediate Similarity	NPC302001
0.7802	Intermediate Similarity	NPC474442
0.7795	Intermediate Similarity	NPC320088
0.7766	Intermediate Similarity	NPC475754
0.7732	Intermediate Similarity	NPC248642
0.7692	Intermediate Similarity	NPC276674
0.7692	Intermediate Similarity	NPC33902
0.7692	Intermediate Similarity	NPC156576
0.768	Intermediate Similarity	NPC179704
0.7668	Intermediate Similarity	NPC320223
0.7668	Intermediate Similarity	NPC190461
0.7668	Intermediate Similarity	NPC114364
0.7629	Intermediate Similarity	NPC126284
0.7617	Intermediate Similarity	NPC287588
0.7604	Intermediate Similarity	NPC228040
0.7585	Intermediate Similarity	NPC46679
0.7565	Intermediate Similarity	NPC128560
0.7565	Intermediate Similarity	NPC229166
0.7565	Intermediate Similarity	NPC199465
0.7559	Intermediate Similarity	NPC108826
0.7552	Intermediate Similarity	NPC168153
0.755	Intermediate Similarity	NPC78284
0.7548	Intermediate Similarity	NPC85661
0.7548	Intermediate Similarity	NPC171882
0.7548	Intermediate Similarity	NPC121510
0.7525	Intermediate Similarity	NPC214116
0.7524	Intermediate Similarity	NPC91234
0.7524	Intermediate Similarity	NPC156728
0.7524	Intermediate Similarity	NPC244606
0.7513	Intermediate Similarity	NPC135772
0.7513	Intermediate Similarity	NPC285941
0.7513	Intermediate Similarity	NPC474051
0.7488	Intermediate Similarity	NPC227361
0.7488	Intermediate Similarity	NPC124658
0.7487	Intermediate Similarity	NPC294790
0.7487	Intermediate Similarity	NPC118633
0.7487	Intermediate Similarity	NPC148693
0.7487	Intermediate Similarity	NPC247389
0.7487	Intermediate Similarity	NPC235628
0.7486	Intermediate Similarity	NPC77359
0.7476	Intermediate Similarity	NPC61731
0.7476	Intermediate Similarity	NPC186569
0.7474	Intermediate Similarity	NPC49353
0.7473	Intermediate Similarity	NPC16436
0.7462	Intermediate Similarity	NPC476575
0.7461	Intermediate Similarity	NPC231371
0.7459	Intermediate Similarity	NPC18614
0.7453	Intermediate Similarity	NPC290227
0.7447	Intermediate Similarity	NPC69360
0.7435	Intermediate Similarity	NPC476432
0.7435	Intermediate Similarity	NPC24264
0.7435	Intermediate Similarity	NPC68328
0.7435	Intermediate Similarity	NPC219341
0.7418	Intermediate Similarity	NPC240684
0.7411	Intermediate Similarity	NPC476574
0.7411	Intermediate Similarity	NPC477561
0.7411	Intermediate Similarity	NPC312918
0.7411	Intermediate Similarity	NPC155442
0.7405	Intermediate Similarity	NPC52475
0.7396	Intermediate Similarity	NPC298979
0.7396	Intermediate Similarity	NPC210918
0.7395	Intermediate Similarity	NPC256422
0.7385	Intermediate Similarity	NPC477558
0.7382	Intermediate Similarity	NPC225774
0.7382	Intermediate Similarity	NPC167546
0.7382	Intermediate Similarity	NPC16805
0.7382	Intermediate Similarity	NPC302527
0.7379	Intermediate Similarity	NPC295676
0.7376	Intermediate Similarity	NPC117717
0.7374	Intermediate Similarity	NPC116284
0.7374	Intermediate Similarity	NPC275132
0.7366	Intermediate Similarity	NPC212163
0.7356	Intermediate Similarity	NPC38961
0.735	Intermediate Similarity	NPC57036
0.7344	Intermediate Similarity	NPC90984
0.7326	Intermediate Similarity	NPC10730
0.7326	Intermediate Similarity	NPC10875
0.7326	Intermediate Similarity	NPC21902
0.7323	Intermediate Similarity	NPC474607
0.7322	Intermediate Similarity	NPC476301
0.7322	Intermediate Similarity	NPC43508
0.732	Intermediate Similarity	NPC474953
0.7313	Intermediate Similarity	NPC186546
0.7313	Intermediate Similarity	NPC476576
0.7306	Intermediate Similarity	NPC81218
0.7306	Intermediate Similarity	NPC306555
0.7306	Intermediate Similarity	NPC117188
0.7306	Intermediate Similarity	NPC205421
0.7306	Intermediate Similarity	NPC304846
0.7306	Intermediate Similarity	NPC12053
0.7306	Intermediate Similarity	NPC158376
0.7306	Intermediate Similarity	NPC474931
0.7306	Intermediate Similarity	NPC145832
0.7299	Intermediate Similarity	NPC168250
0.7296	Intermediate Similarity	NPC187678
0.7294	Intermediate Similarity	NPC118121
0.7292	Intermediate Similarity	NPC54125
0.7292	Intermediate Similarity	NPC89199
0.7286	Intermediate Similarity	NPC474650
0.7282	Intermediate Similarity	NPC19520
0.7282	Intermediate Similarity	NPC149090
0.7277	Intermediate Similarity	NPC82763
0.7269	Intermediate Similarity	NPC204446
0.7268	Intermediate Similarity	NPC182257
0.7268	Intermediate Similarity	NPC217635
0.7268	Intermediate Similarity	NPC79429
0.7268	Intermediate Similarity	NPC471667
0.7258	Intermediate Similarity	NPC44452
0.7245	Intermediate Similarity	NPC2314
0.7243	Intermediate Similarity	NPC213074
0.7243	Intermediate Similarity	NPC224674
0.7243	Intermediate Similarity	NPC275284
0.7243	Intermediate Similarity	NPC193473
0.7243	Intermediate Similarity	NPC114505
0.7243	Intermediate Similarity	NPC31325
0.7243	Intermediate Similarity	NPC15956
0.724	Intermediate Similarity	NPC19555
0.7236	Intermediate Similarity	NPC32413
0.7236	Intermediate Similarity	NPC474506
0.7233	Intermediate Similarity	NPC23080
0.7233	Intermediate Similarity	NPC193906
0.7231	Intermediate Similarity	NPC152212
0.7231	Intermediate Similarity	NPC6152
0.7225	Intermediate Similarity	NPC266753
0.7225	Intermediate Similarity	NPC232924
0.7225	Intermediate Similarity	NPC160298
0.7225	Intermediate Similarity	NPC306902
0.7225	Intermediate Similarity	NPC477559
0.7219	Intermediate Similarity	NPC98624
0.7219	Intermediate Similarity	NPC183380
0.7216	Intermediate Similarity	NPC310894
0.7216	Intermediate Similarity	NPC150879
0.7202	Intermediate Similarity	NPC253043
0.7202	Intermediate Similarity	NPC196447
0.7202	Intermediate Similarity	NPC212794
0.7202	Intermediate Similarity	NPC96603
0.7202	Intermediate Similarity	NPC136508
0.7202	Intermediate Similarity	NPC477563
0.7202	Intermediate Similarity	NPC13504
0.7202	Intermediate Similarity	NPC306843
0.7202	Intermediate Similarity	NPC78222
0.7196	Intermediate Similarity	NPC78809
0.7186	Intermediate Similarity	NPC258695
0.7186	Intermediate Similarity	NPC193377
0.7186	Intermediate Similarity	NPC470879
0.7186	Intermediate Similarity	NPC267408
0.7186	Intermediate Similarity	NPC475794
0.7178	Intermediate Similarity	NPC474661
0.7178	Intermediate Similarity	NPC475919
0.7177	Intermediate Similarity	NPC311357
0.7172	Intermediate Similarity	NPC471921
0.7172	Intermediate Similarity	NPC129930
0.7172	Intermediate Similarity	NPC471922
0.7172	Intermediate Similarity	NPC1291
0.7172	Intermediate Similarity	NPC115343
0.7172	Intermediate Similarity	NPC292712
0.7172	Intermediate Similarity	NPC20114
0.7172	Intermediate Similarity	NPC474075
0.7172	Intermediate Similarity	NPC471920
0.7172	Intermediate Similarity	NPC114550
0.7172	Intermediate Similarity	NPC312006
0.7165	Intermediate Similarity	NPC198741
0.7158	Intermediate Similarity	NPC60249
0.7157	Intermediate Similarity	NPC289743
0.7157	Intermediate Similarity	NPC110374
0.7157	Intermediate Similarity	NPC66341
0.7157	Intermediate Similarity	NPC192135
0.7157	Intermediate Similarity	NPC477020
0.7151	Intermediate Similarity	NPC471032
0.7151	Intermediate Similarity	NPC470935
0.715	Intermediate Similarity	NPC324144
0.715	Intermediate Similarity	NPC1229
0.7143	Intermediate Similarity	NPC227033
0.7143	Intermediate Similarity	NPC237579
0.7136	Intermediate Similarity	NPC23219
0.7135	Intermediate Similarity	NPC286245
0.7135	Intermediate Similarity	NPC272619
0.713	Intermediate Similarity	NPC235076
0.7128	Intermediate Similarity	NPC181653

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 NPC159101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	712
0.2-0.3	1016
0.3-0.4	2320
0.4-0.5	2623
0.5-0.6	1736
0.6-0.7	414
0.7-0.8	18
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
0.7259	Intermediate Similarity	NPD6184	Discontinued
0.7254	Intermediate Similarity	NPD3051	Approved
0.7228	Intermediate Similarity	NPD2843	Phase 2
0.7228	Intermediate Similarity	NPD2845	Phase 2
0.7216	Intermediate Similarity	NPD2969	Approved
0.7216	Intermediate Similarity	NPD2970	Approved
0.7181	Intermediate Similarity	NPD3296	Phase 1
0.7178	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD8067	Phase 3
0.7129	Intermediate Similarity	NPD4663	Approved
0.7128	Intermediate Similarity	NPD5811	Approved
0.712	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6674	Discontinued
0.7092	Intermediate Similarity	NPD27	Approved
0.7092	Intermediate Similarity	NPD2489	Approved
0.7078	Intermediate Similarity	NPD3763	Approved
0.7065	Intermediate Similarity	NPD4577	Approved
0.7065	Intermediate Similarity	NPD4578	Approved
0.7056	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3778	Approved
0.7044	Intermediate Similarity	NPD4951	Discontinued
0.7039	Intermediate Similarity	NPD7262	Phase 1
0.7021	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7313	Approved
0.698	Remote Similarity	NPD7312	Approved
0.698	Remote Similarity	NPD7311	Approved
0.698	Remote Similarity	NPD7310	Approved
0.6976	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3453	Discontinued
0.6946	Remote Similarity	NPD7309	Approved
0.6911	Remote Similarity	NPD5617	Suspended
0.689	Remote Similarity	NPD5582	Discontinued
0.6875	Remote Similarity	NPD7125	Discontinued
0.6857	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6723	Discontinued
0.6854	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4481	Phase 3
0.6832	Remote Similarity	NPD7007	Discovery
0.6825	Remote Similarity	NPD4123	Phase 3
0.6814	Remote Similarity	NPD7546	Discontinued
0.6806	Remote Similarity	NPD2883	Discontinued
0.6806	Remote Similarity	NPD4003	Phase 3
0.6794	Remote Similarity	NPD5150	Phase 2
0.6792	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3236	Phase 3
0.6786	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4083	Discontinued
0.6783	Remote Similarity	NPD6494	Phase 2
0.6771	Remote Similarity	NPD4005	Discontinued
0.6769	Remote Similarity	NPD2563	Approved
0.6769	Remote Similarity	NPD2560	Approved
0.6768	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6842	Approved
0.6763	Remote Similarity	NPD6841	Approved
0.6763	Remote Similarity	NPD6843	Phase 3
0.6763	Remote Similarity	NPD3349	Phase 2
0.6749	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4675	Approved
0.6736	Remote Similarity	NPD4678	Approved
0.6735	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6071	Discontinued
0.6734	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3452	Approved
0.6729	Remote Similarity	NPD3450	Approved
0.6727	Remote Similarity	NPD7827	Phase 1
0.6727	Remote Similarity	NPD3815	Phase 1
0.6727	Remote Similarity	NPD3816	Phase 1
0.672	Remote Similarity	NPD1375	Discontinued
0.6714	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4108	Discontinued
0.6702	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6331	Phase 2
0.6701	Remote Similarity	NPD5604	Discontinued
0.6701	Remote Similarity	NPD4055	Discovery
0.67	Remote Similarity	NPD3920	Phase 2
0.6699	Remote Similarity	NPD8053	Approved
0.6699	Remote Similarity	NPD8054	Approved
0.6698	Remote Similarity	NPD4604	Approved
0.6698	Remote Similarity	NPD4605	Approved
0.6684	Remote Similarity	NPD6063	Approved
0.6683	Remote Similarity	NPD7228	Approved
0.6683	Remote Similarity	NPD3398	Discontinued
0.6667	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2161	Phase 2
0.6651	Remote Similarity	NPD2494	Approved
0.6651	Remote Similarity	NPD2493	Approved
0.6651	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4966	Approved
0.665	Remote Similarity	NPD4965	Approved
0.665	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4967	Phase 2
0.6634	Remote Similarity	NPD5938	Phase 3
0.6633	Remote Similarity	NPD5773	Approved
0.6633	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5772	Approved
0.6633	Remote Similarity	NPD1850	Phase 3
0.6625	Remote Similarity	NPD8367	Approved
0.6622	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4859	Phase 1
0.662	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2974	Approved
0.662	Remote Similarity	NPD2973	Approved
0.662	Remote Similarity	NPD2975	Approved
0.6619	Remote Similarity	NPD2488	Approved
0.6619	Remote Similarity	NPD2490	Approved
0.6619	Remote Similarity	NPD5641	Discontinued
0.6603	Remote Similarity	NPD5800	Discontinued
0.66	Remote Similarity	NPD7199	Phase 2
0.659	Remote Similarity	NPD4004	Approved
0.659	Remote Similarity	NPD4002	Approved
0.6587	Remote Similarity	NPD6339	Approved
0.6587	Remote Similarity	NPD6340	Approved
0.6584	Remote Similarity	NPD8492	Approved
0.6583	Remote Similarity	NPD6234	Discontinued
0.6582	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD37	Approved
0.6579	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5429	Discontinued
0.657	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8156	Discontinued
0.656	Remote Similarity	NPD4582	Approved
0.656	Remote Similarity	NPD4583	Approved
0.655	Remote Similarity	NPD6037	Discontinued
0.6548	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2978	Approved
0.6548	Remote Similarity	NPD8455	Phase 2
0.6548	Remote Similarity	NPD5929	Approved
0.6548	Remote Similarity	NPD2977	Approved
0.6545	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7034	Discontinued
0.6535	Remote Similarity	NPD2215	Approved
0.6535	Remote Similarity	NPD2216	Approved
0.6533	Remote Similarity	NPD5164	Discontinued
0.6533	Remote Similarity	NPD7831	Phase 2
0.6533	Remote Similarity	NPD7833	Phase 2
0.6533	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7169	Suspended
0.6528	Remote Similarity	NPD4580	Approved
0.6526	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8252	Approved
0.652	Remote Similarity	NPD8099	Discontinued
0.652	Remote Similarity	NPD8251	Approved
0.6518	Remote Similarity	NPD5903	Approved
0.6518	Remote Similarity	NPD5902	Approved
0.6517	Remote Similarity	NPD2821	Approved
0.6516	Remote Similarity	NPD8151	Discontinued
0.6512	Remote Similarity	NPD6877	Discontinued
0.651	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7222	Phase 2
0.65	Remote Similarity	NPD7263	Phase 2
0.6496	Remote Similarity	NPD6625	Approved
0.6495	Remote Similarity	NPD6031	Approved
0.6495	Remote Similarity	NPD6030	Approved
0.6492	Remote Similarity	NPD5241	Discontinued
0.649	Remote Similarity	NPD2968	Approved
0.649	Remote Similarity	NPD2971	Approved
0.6489	Remote Similarity	NPD7047	Phase 3
0.6488	Remote Similarity	NPD5844	Phase 1
0.6488	Remote Similarity	NPD5810	Discontinued
0.6482	Remote Similarity	NPD7773	Phase 2
0.6474	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7240	Approved
0.6463	Remote Similarity	NPD6997	Phase 2
0.6462	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4502	Phase 2
0.6456	Remote Similarity	NPD7479	Phase 2
0.6455	Remote Similarity	NPD5530	Phase 1
0.6453	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6612	Phase 2
0.6447	Remote Similarity	NPD2789	Approved
0.6439	Remote Similarity	NPD3909	Discontinued
0.6435	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4420	Approved
0.6432	Remote Similarity	NPD7395	Discontinued
0.6432	Remote Similarity	NPD3924	Approved
0.6432	Remote Similarity	NPD3921	Approved
0.6432	Remote Similarity	NPD3923	Approved
0.6432	Remote Similarity	NPD3922	Approved
0.6425	Remote Similarity	NPD2420	Approved
0.6425	Remote Similarity	NPD6296	Discontinued
0.6425	Remote Similarity	NPD2421	Approved
0.6425	Remote Similarity	NPD7584	Approved
0.6414	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2122	Discontinued
0.6408	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6874	Approved
0.6398	Remote Similarity	NPD1613	Approved
0.6398	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD8461	Discontinued
0.6396	Remote Similarity	NPD6502	Phase 2
0.6394	Remote Similarity	NPD6559	Discontinued
0.6393	Remote Similarity	NPD6823	Phase 2
0.6392	Remote Similarity	NPD4584	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