NPASS Compound

Structure

NPC61731 OpenBabel07101718222D 39 43 0 0 1 0 0 0 0 0999 V2000 -9.9207 4.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9580 4.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8128 3.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8128 2.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4393 5.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0743 2.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3833 5.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3273 3.5524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4953 5.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3833 1.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9664 3.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9664 1.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5514 3.5524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4953 1.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7263 3.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 0.6539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4393 0.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3975 -0.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0743 4.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8043 4.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4393 1.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1201 3.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8043 2.6085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1201 2.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 1.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5726 3.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5726 0.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5726 2.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7263 1.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7263 0.6539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1116 2.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 3.5857 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5930 0.1986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1116 3.5857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 4.5630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2653 3.0971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 -0.7906 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 -4.9580 2.1198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 19 2 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 24 2 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 26 2 0 0 0 0 16 25 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 33 2 0 0 0 0 18 37 1 0 0 0 0 18 38 1 0 0 0 0 22 24 1 0 0 0 0 23 39 1 1 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 30 2 0 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 29 30 1 0 0 0 0 30 38 1 0 0 0 0 31 34 2 0 0 0 0 31 39 1 0 0 0 0 32 35 2 0 0 0 0 32 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	527.19
Volume:	540.204
LogP:	6.723
LogD:	4.798
LogS:	-7.431
# Rotatable Bonds:	5
TPSA:	104.97
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	4.36
Fsp3:	0.29
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	2.8349391868687235e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	100.67522430419922%
Volume Distribution (VD):	0.247
Pgp-substrate:	1.2227327823638916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.744
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.935
CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	4.441
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.891
Drug-inuced Liver Injury (DILI):	0.852
AMES Toxicity:	0.981
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.966
Carcinogencity:	0.901
Eye Corrosion:	0.004
Eye Irritation:	0.365
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC61731

Natural Product ID:	NPC61731
*Common Name:**	Aristoloterpenate-Ii
IUPAC Name:	[(1R,2Z,6E,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl] 6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylate
Synonyms:	Aristoloterpenate-II
Standard InCHIKey:	XJBILGKCOVAJTM-AJNUOSSRSA-N
Standard InCHI:	InChI=1S/C31H29NO7/c1-19-7-5-9-20(2)13-23(14-21(17-33)10-6-8-19)39-31(34)25-16-27-30(38-18-37-27)29-24-12-4-3-11-22(24)15-26(28(25)29)32(35)36/h3-4,8-9,11-12,14-17,23H,5-7,10,13,18H2,1-2H3/b19-8+,20-9+,21-14-/t23-/m1/s1
SMILES:	C/C/1=CCC/C(=C/[C@@H](C/C(=C/CC1)/C)OC(=O)c1cc2c(c3c4ccccc4cc(c13)N(=O)=O)OCO2)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463405
PubChem CID:	10346826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0002664] Aristolochic acids 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
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075784]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	root	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	root and stem	n.a.	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	stem	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16163	Aristolochia heterophylla	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8230.0	nM	PMID[454250]

☑ 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 NPC61731 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	437
0.1-0.2	2074
0.2-0.3	5546
0.3-0.4	11938
0.4-0.5	5678
0.5-0.6	12274
0.6-0.7	4618
0.7-0.8	116
0.8-0.85	0
0.85-0.9	1
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186569
0.9894	High Similarity	NPC124658
0.9894	High Similarity	NPC227361
0.9679	High Similarity	NPC38961
0.9639	High Similarity	NPC256422
0.9476	High Similarity	NPC85661
0.9424	High Similarity	NPC46679
0.9375	High Similarity	NPC121510
0.9375	High Similarity	NPC171882
0.9231	High Similarity	NPC91234
0.9137	High Similarity	NPC290227
0.9091	High Similarity	NPC240684
0.801	Intermediate Similarity	NPC90185
0.7952	Intermediate Similarity	NPC55470
0.7729	Intermediate Similarity	NPC207971
0.7701	Intermediate Similarity	NPC118332
0.7667	Intermediate Similarity	NPC100573
0.7667	Intermediate Similarity	NPC207873
0.7662	Intermediate Similarity	NPC296742
0.7619	Intermediate Similarity	NPC222561
0.7619	Intermediate Similarity	NPC308943
0.7612	Intermediate Similarity	NPC224293
0.7608	Intermediate Similarity	NPC268077
0.7574	Intermediate Similarity	NPC312531
0.7574	Intermediate Similarity	NPC112676
0.7573	Intermediate Similarity	NPC23080
0.7573	Intermediate Similarity	NPC193906
0.7562	Intermediate Similarity	NPC69213
0.7552	Intermediate Similarity	NPC125713
0.7539	Intermediate Similarity	NPC109765
0.7539	Intermediate Similarity	NPC115123
0.7539	Intermediate Similarity	NPC239113
0.75	Intermediate Similarity	NPC202495
0.7476	Intermediate Similarity	NPC159101
0.7452	Intermediate Similarity	NPC5374
0.7435	Intermediate Similarity	NPC54179
0.7427	Intermediate Similarity	NPC29472
0.7423	Intermediate Similarity	NPC78944
0.7409	Intermediate Similarity	NPC19600
0.7404	Intermediate Similarity	NPC71124
0.74	Intermediate Similarity	NPC260118
0.7379	Intermediate Similarity	NPC254957
0.7376	Intermediate Similarity	NPC249405
0.7373	Intermediate Similarity	NPC298449
0.7363	Intermediate Similarity	NPC192939
0.7363	Intermediate Similarity	NPC215747
0.7354	Intermediate Similarity	NPC127827
0.735	Intermediate Similarity	NPC265383
0.7347	Intermediate Similarity	NPC116838
0.7347	Intermediate Similarity	NPC22130
0.7323	Intermediate Similarity	NPC471923
0.7316	Intermediate Similarity	NPC300983
0.7316	Intermediate Similarity	NPC475722
0.7296	Intermediate Similarity	NPC15212
0.7291	Intermediate Similarity	NPC28425
0.7286	Intermediate Similarity	NPC473531
0.7286	Intermediate Similarity	NPC475453
0.7282	Intermediate Similarity	NPC474043
0.7268	Intermediate Similarity	NPC474009
0.7241	Intermediate Similarity	NPC179704
0.7241	Intermediate Similarity	NPC119579
0.7228	Intermediate Similarity	NPC190461
0.7222	Intermediate Similarity	NPC46990
0.722	Intermediate Similarity	NPC180253
0.722	Intermediate Similarity	NPC219170
0.7216	Intermediate Similarity	NPC234730
0.7214	Intermediate Similarity	NPC52598
0.7212	Intermediate Similarity	NPC302001
0.7206	Intermediate Similarity	NPC276060
0.7192	Intermediate Similarity	NPC311936
0.7186	Intermediate Similarity	NPC477884
0.7179	Intermediate Similarity	NPC261484
0.7178	Intermediate Similarity	NPC471921
0.7178	Intermediate Similarity	NPC129930
0.7178	Intermediate Similarity	NPC471922
0.7178	Intermediate Similarity	NPC287588
0.7178	Intermediate Similarity	NPC20114
0.7178	Intermediate Similarity	NPC474075
0.7178	Intermediate Similarity	NPC473697
0.7178	Intermediate Similarity	NPC471920
0.7178	Intermediate Similarity	NPC312006
0.7178	Intermediate Similarity	NPC114550
0.7178	Intermediate Similarity	NPC292712
0.7173	Intermediate Similarity	NPC24193
0.7172	Intermediate Similarity	NPC19948
0.7172	Intermediate Similarity	NPC198796
0.7157	Intermediate Similarity	NPC196771
0.7156	Intermediate Similarity	NPC46744
0.7156	Intermediate Similarity	NPC14622
0.7156	Intermediate Similarity	NPC70290
0.7156	Intermediate Similarity	NPC124302
0.7156	Intermediate Similarity	NPC73020
0.7156	Intermediate Similarity	NPC215098
0.715	Intermediate Similarity	NPC474042
0.715	Intermediate Similarity	NPC474904
0.715	Intermediate Similarity	NPC174734
0.7149	Intermediate Similarity	NPC227033
0.7143	Intermediate Similarity	NPC143328
0.7143	Intermediate Similarity	NPC184624
0.7143	Intermediate Similarity	NPC470023
0.7143	Intermediate Similarity	NPC76458
0.7143	Intermediate Similarity	NPC82733
0.7121	Intermediate Similarity	NPC191352
0.7121	Intermediate Similarity	NPC258322
0.7121	Intermediate Similarity	NPC319749
0.712	Intermediate Similarity	NPC181464
0.7114	Intermediate Similarity	NPC227683
0.711	Intermediate Similarity	NPC25961
0.7109	Intermediate Similarity	NPC470021
0.7108	Intermediate Similarity	NPC27887
0.7108	Intermediate Similarity	NPC193377
0.7107	Intermediate Similarity	NPC15764
0.7107	Intermediate Similarity	NPC68619
0.7107	Intermediate Similarity	NPC325122
0.7101	Intermediate Similarity	NPC22928
0.7094	Intermediate Similarity	NPC35680
0.7094	Intermediate Similarity	NPC85613
0.7092	Intermediate Similarity	NPC473900
0.7092	Intermediate Similarity	NPC301897
0.7089	Intermediate Similarity	NPC72788
0.7089	Intermediate Similarity	NPC120671
0.7089	Intermediate Similarity	NPC226652
0.7089	Intermediate Similarity	NPC314100
0.7085	Intermediate Similarity	NPC280778
0.7079	Intermediate Similarity	NPC117911
0.7079	Intermediate Similarity	NPC285941
0.7071	Intermediate Similarity	NPC65784
0.7071	Intermediate Similarity	NPC139876
0.7069	Intermediate Similarity	NPC189903
0.7069	Intermediate Similarity	NPC182907
0.7068	Intermediate Similarity	NPC24257
0.7068	Intermediate Similarity	NPC153620
0.7067	Intermediate Similarity	NPC237579
0.7062	Intermediate Similarity	NPC33256
0.7056	Intermediate Similarity	NPC167098
0.7056	Intermediate Similarity	NPC476220
0.7056	Intermediate Similarity	NPC160113
0.7056	Intermediate Similarity	NPC296044
0.705	Intermediate Similarity	NPC247389
0.7039	Intermediate Similarity	NPC35266
0.7037	Intermediate Similarity	NPC125134
0.7037	Intermediate Similarity	NPC137920
0.7037	Intermediate Similarity	NPC244606
0.7037	Intermediate Similarity	NPC156728
0.7037	Intermediate Similarity	NPC86455
0.7035	Intermediate Similarity	NPC469889
0.7035	Intermediate Similarity	NPC296540
0.7035	Intermediate Similarity	NPC109238
0.7035	Intermediate Similarity	NPC309335
0.703	Intermediate Similarity	NPC67978
0.703	Intermediate Similarity	NPC303581
0.7026	Intermediate Similarity	NPC108342
0.7026	Intermediate Similarity	NPC154922
0.7023	Intermediate Similarity	NPC328700
0.7023	Intermediate Similarity	NPC119818
0.7023	Intermediate Similarity	NPC2173
0.7023	Intermediate Similarity	NPC202771
0.7015	Intermediate Similarity	NPC474301
0.7015	Intermediate Similarity	NPC41689
0.701	Intermediate Similarity	NPC283810
0.701	Intermediate Similarity	NPC5167
0.7005	Intermediate Similarity	NPC275690
0.7005	Intermediate Similarity	NPC161609
0.7	Intermediate Similarity	NPC476432
0.7	Intermediate Similarity	NPC24264
0.7	Intermediate Similarity	NPC219341
0.6995	Remote Similarity	NPC17677
0.699	Remote Similarity	NPC273578
0.6986	Remote Similarity	NPC141440
0.6981	Remote Similarity	NPC162653
0.698	Remote Similarity	NPC83049
0.698	Remote Similarity	NPC320471
0.698	Remote Similarity	NPC118162
0.6977	Remote Similarity	NPC311781
0.6976	Remote Similarity	NPC316539
0.6976	Remote Similarity	NPC477881
0.6974	Remote Similarity	NPC104353
0.6968	Remote Similarity	NPC477827
0.6968	Remote Similarity	NPC477826
0.6965	Remote Similarity	NPC308156
0.6963	Remote Similarity	NPC471305
0.6963	Remote Similarity	NPC212163
0.6962	Remote Similarity	NPC124313
0.6961	Remote Similarity	NPC308267
0.6959	Remote Similarity	NPC474305
0.6959	Remote Similarity	NPC261322
0.6954	Remote Similarity	NPC472835
0.6954	Remote Similarity	NPC3273
0.695	Remote Similarity	NPC209411
0.695	Remote Similarity	NPC239890
0.695	Remote Similarity	NPC225774
0.695	Remote Similarity	NPC167546
0.695	Remote Similarity	NPC16805
0.695	Remote Similarity	NPC131905
0.695	Remote Similarity	NPC302527
0.6946	Remote Similarity	NPC311912
0.6946	Remote Similarity	NPC79322
0.694	Remote Similarity	NPC22481
0.6939	Remote Similarity	NPC308555
0.6938	Remote Similarity	NPC320088

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 NPC61731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	884
0.2-0.3	1101
0.3-0.4	2568
0.4-0.5	2551
0.5-0.6	1406
0.6-0.7	298
0.7-0.8	12
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
0.7389	Intermediate Similarity	NPD6723	Discontinued
0.7371	Intermediate Similarity	NPD6296	Discontinued
0.7245	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4420	Approved
0.7149	Intermediate Similarity	NPD8067	Phase 3
0.7107	Intermediate Similarity	NPD3252	Approved
0.7089	Intermediate Similarity	NPD4107	Approved
0.7087	Intermediate Similarity	NPD6625	Approved
0.707	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5005	Approved
0.7023	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5006	Approved
0.7018	Intermediate Similarity	NPD4859	Phase 1
0.7009	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4482	Phase 3
0.6971	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5844	Phase 1
0.6888	Remote Similarity	NPD6386	Approved
0.6888	Remote Similarity	NPD6385	Approved
0.6881	Remote Similarity	NPD5242	Approved
0.6866	Remote Similarity	NPD2821	Approved
0.6856	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6232	Discontinued
0.6829	Remote Similarity	NPD1221	Approved
0.6827	Remote Similarity	NPD7546	Discontinued
0.6825	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7476	Discontinued
0.6816	Remote Similarity	NPD3251	Approved
0.6812	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5950	Discontinued
0.6745	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7473	Discontinued
0.6726	Remote Similarity	NPD5914	Approved
0.6712	Remote Similarity	NPD3057	Approved
0.6709	Remote Similarity	NPD4846	Phase 2
0.6698	Remote Similarity	NPD7256	Discontinued
0.6683	Remote Similarity	NPD1220	Phase 1
0.6683	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD2968	Approved
0.6653	Remote Similarity	NPD7922	Phase 1
0.6652	Remote Similarity	NPD7891	Discontinued
0.6636	Remote Similarity	NPD3533	Approved
0.6636	Remote Similarity	NPD2972	Approved
0.6623	Remote Similarity	NPD5980	Discovery
0.6621	Remote Similarity	NPD3289	Phase 3
0.6621	Remote Similarity	NPD3290	Approved
0.662	Remote Similarity	NPD3398	Discontinued
0.6618	Remote Similarity	NPD7177	Discontinued
0.6609	Remote Similarity	NPD3437	Discontinued
0.6602	Remote Similarity	NPD4481	Phase 3
0.6601	Remote Similarity	NPD6234	Discontinued
0.6597	Remote Similarity	NPD3752	Phase 2
0.6597	Remote Similarity	NPD2438	Suspended
0.6596	Remote Similarity	NPD2979	Phase 3
0.6595	Remote Similarity	NPD7278	Phase 2
0.6595	Remote Similarity	NPD7279	Phase 2
0.6574	Remote Similarity	NPD6213	Phase 3
0.6574	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6212	Phase 3
0.6571	Remote Similarity	NPD7039	Approved
0.6571	Remote Similarity	NPD6559	Discontinued
0.6571	Remote Similarity	NPD8367	Approved
0.6571	Remote Similarity	NPD7038	Approved
0.6569	Remote Similarity	NPD5494	Approved
0.6567	Remote Similarity	NPD4505	Phase 1
0.6565	Remote Similarity	NPD5519	Discontinued
0.6561	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3448	Approved
0.6561	Remote Similarity	NPD7627	Approved
0.6561	Remote Similarity	NPD7626	Approved
0.6561	Remote Similarity	NPD2491	Approved
0.656	Remote Similarity	NPD2973	Approved
0.656	Remote Similarity	NPD2974	Approved
0.656	Remote Similarity	NPD2975	Approved
0.6549	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7783	Phase 2
0.6538	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD2247	Approved
0.6537	Remote Similarity	NPD6457	Approved
0.6537	Remote Similarity	NPD2249	Approved
0.6537	Remote Similarity	NPD7199	Phase 2
0.6537	Remote Similarity	NPD8127	Discontinued
0.6535	Remote Similarity	NPD5978	Approved
0.6535	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5977	Approved
0.6535	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.653	Remote Similarity	NPD5071	Phase 2
0.6526	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3912	Discontinued
0.652	Remote Similarity	NPD7827	Phase 1
0.6517	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7907	Approved
0.6507	Remote Similarity	NPD5025	Approved
0.65	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7708	Approved
0.6476	Remote Similarity	NPD5676	Approved
0.6473	Remote Similarity	NPD7999	Approved
0.6473	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4580	Approved
0.6466	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8492	Approved
0.6465	Remote Similarity	NPD1898	Discontinued
0.646	Remote Similarity	NPD8151	Discontinued
0.6459	Remote Similarity	NPD3818	Discontinued
0.645	Remote Similarity	NPD7458	Discontinued
0.6445	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2494	Approved
0.6441	Remote Similarity	NPD2493	Approved
0.6441	Remote Similarity	NPD3450	Approved
0.6441	Remote Similarity	NPD3452	Approved
0.6439	Remote Similarity	NPD919	Approved
0.6438	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3965	Phase 1
0.6425	Remote Similarity	NPD6874	Approved
0.6422	Remote Similarity	NPD4665	Approved
0.6422	Remote Similarity	NPD4111	Phase 1
0.6422	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6997	Phase 2
0.6406	Remote Similarity	NPD2490	Approved
0.6406	Remote Similarity	NPD2488	Approved
0.6403	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6782	Approved
0.6396	Remote Similarity	NPD6780	Approved
0.6396	Remote Similarity	NPD6781	Approved
0.6396	Remote Similarity	NPD6777	Approved
0.6396	Remote Similarity	NPD6778	Approved
0.6396	Remote Similarity	NPD6779	Approved
0.6396	Remote Similarity	NPD6776	Approved
0.6392	Remote Similarity	NPD7803	Approved
0.6386	Remote Similarity	NPD2672	Discontinued
0.6385	Remote Similarity	NPD1891	Discontinued
0.6381	Remote Similarity	NPD7228	Approved
0.6377	Remote Similarity	NPD2681	Approved
0.6377	Remote Similarity	NPD2680	Approved
0.6376	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7583	Approved
0.6368	Remote Similarity	NPD6184	Discontinued
0.6364	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5582	Discontinued
0.6364	Remote Similarity	NPD8149	Discontinued
0.6364	Remote Similarity	NPD7047	Phase 3
0.6356	Remote Similarity	NPD7870	Phase 2
0.6356	Remote Similarity	NPD4582	Approved
0.6356	Remote Similarity	NPD7871	Phase 2
0.6356	Remote Similarity	NPD4583	Approved
0.6355	Remote Similarity	NPD8313	Approved
0.6355	Remote Similarity	NPD8312	Approved
0.6351	Remote Similarity	NPD8285	Discontinued
0.6348	Remote Similarity	NPD4356	Discontinued
0.6348	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7585	Approved
0.6337	Remote Similarity	NPD3684	Discontinued
0.6336	Remote Similarity	NPD8404	Phase 2
0.6332	Remote Similarity	NPD683	Approved
0.6329	Remote Similarity	NPD7224	Discontinued
0.6329	Remote Similarity	NPD7223	Discontinued
0.6327	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3349	Phase 2
0.6311	Remote Similarity	NPD7696	Phase 3
0.6311	Remote Similarity	NPD7435	Discontinued
0.6311	Remote Similarity	NPD7698	Approved
0.6311	Remote Similarity	NPD7497	Discontinued
0.6311	Remote Similarity	NPD4004	Approved
0.6311	Remote Similarity	NPD7697	Approved
0.6311	Remote Similarity	NPD4002	Approved
0.6305	Remote Similarity	NPD6873	Phase 2
0.6304	Remote Similarity	NPD7225	Discontinued
0.6303	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.63	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7584	Approved
0.6298	Remote Similarity	NPD1247	Approved
0.6296	Remote Similarity	NPD5805	Approved
0.6296	Remote Similarity	NPD7048	Phase 3
0.6295	Remote Similarity	NPD6321	Discontinued
0.6294	Remote Similarity	NPD4628	Phase 3
0.6293	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7874	Approved
0.6288	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3226	Approved
0.6287	Remote Similarity	NPD5811	Approved
0.6282	Remote Similarity	NPD2899	Discontinued
0.6281	Remote Similarity	NPD6758	Approved
0.6273	Remote Similarity	NPD7125	Discontinued
0.6268	Remote Similarity	NPD3051	Approved
0.6262	Remote Similarity	NPD7240	Approved
0.6262	Remote Similarity	NPD7685	Pre-registration
0.6261	Remote Similarity	NPD5564	Approved
0.6256	Remote Similarity	NPD5525	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