NPASS Compound

Structure

CID35680 OpenBabel06191715362D 23 26 0 0 1 0 0 0 0 0999 V2000 1.2708 -3.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 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 1.9400 -2.9781 0.0000 N 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 19 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 13 5 1 6 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 11 1 6 0 0 0 16 17 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.15
Volume:	318.634
LogP:	2.643
LogD:	2.157
LogS:	-3.653
# Rotatable Bonds:	2
TPSA:	48.0
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	3.841
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.556
MDCK Permeability:	3.175101664965041e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	71.71782684326172%
Volume Distribution (VD):	1.881
Pgp-substrate:	23.51943016052246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.701
CYP2D6-inhibitor:	0.583
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.688

ADMET: Excretion

Clearance (CL):	12.442
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.285
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.042
Carcinogencity:	0.907
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC35680

Natural Product ID:	NPC35680
*Common Name:**	Homolycorine
IUPAC Name:	(5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
Synonyms:	Homolycorine
Standard InCHIKey:	WXZAKVLYZHWSNF-KBRIMQKVSA-N
Standard InCHI:	InChI=1S/C18H21NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-17H,5-7H2,1-3H3/p+1/t13-,16-,17-/m1/s1
SMILES:	C[NH+]1CCC2=CC[C@@H]3[C@@H](c4cc(c(cc4C(=O)O3)OC)OC)[C@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221973
PubChem CID:	160473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004122] Homolycorine-type amaryllidaceae alkaloids

*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
NPO11205	Cassia sieberiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[21070009]
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]
NPO7488	Achillea wilsoniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7488	Achillea wilsoniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11205	Cassia sieberiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11205	Cassia sieberiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7488	Achillea wilsoniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12145	Echinometra lucunter	Species	Echinometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16431	Perezia runcinata	Species	Pereziidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17432	Ligularia przewalskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15516	Linum perenne	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7488	Achillea wilsoniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13863	Ephedra vulgaris	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13181	Ferula persica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26299	Reticularia lycoperdon	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19610	Stachys aegyptiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15141	Polystichum polyblepharum	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17180	Juniperus procera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11205	Cassia sieberiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13711	Liolophura japonica	Species	Chitonidae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	IC50	=	20800.0	nM	PMID[519041]
NPT2468	Cell Line	G-361	Homo sapiens	IC50	=	32900.0	nM	PMID[519041]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[519041]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[519041]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	19400.0	nM	PMID[519041]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	15000.0	nM	PMID[519041]

☑ 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 NPC35680 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	262
0.1-0.2	1234
0.2-0.3	3629
0.3-0.4	9752
0.4-0.5	8455
0.5-0.6	8943
0.6-0.7	9700
0.7-0.8	651
0.8-0.85	59
0.85-0.9	6
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9581	High Similarity	NPC162694
0.9249	High Similarity	NPC33256
0.907	High Similarity	NPC141440
0.9023	High Similarity	NPC94499
0.8689	High Similarity	NPC80472
0.8614	High Similarity	NPC26353
0.8525	High Similarity	NPC286135
0.848	Intermediate Similarity	NPC474708
0.8462	Intermediate Similarity	NPC35345
0.843	Intermediate Similarity	NPC227683
0.8421	Intermediate Similarity	NPC475845
0.8363	Intermediate Similarity	NPC474324
0.8363	Intermediate Similarity	NPC57812
0.8315	Intermediate Similarity	NPC214629
0.8284	Intermediate Similarity	NPC4304
0.8276	Intermediate Similarity	NPC329992
0.827	Intermediate Similarity	NPC311781
0.8268	Intermediate Similarity	NPC230098
0.8207	Intermediate Similarity	NPC124302
0.8207	Intermediate Similarity	NPC14622
0.8207	Intermediate Similarity	NPC215098
0.8207	Intermediate Similarity	NPC73020
0.8207	Intermediate Similarity	NPC46744
0.8207	Intermediate Similarity	NPC70290
0.8192	Intermediate Similarity	NPC474745
0.814	Intermediate Similarity	NPC180306
0.8136	Intermediate Similarity	NPC474325
0.8128	Intermediate Similarity	NPC119818
0.8128	Intermediate Similarity	NPC328700
0.8128	Intermediate Similarity	NPC2173
0.8128	Intermediate Similarity	NPC202771
0.8125	Intermediate Similarity	NPC304675
0.8118	Intermediate Similarity	NPC72788
0.8118	Intermediate Similarity	NPC314100
0.8118	Intermediate Similarity	NPC120671
0.8118	Intermediate Similarity	NPC226652
0.8098	Intermediate Similarity	NPC174783
0.8095	Intermediate Similarity	NPC476500
0.8092	Intermediate Similarity	NPC474858
0.8079	Intermediate Similarity	NPC237044
0.8056	Intermediate Similarity	NPC475981
0.8056	Intermediate Similarity	NPC474746
0.8045	Intermediate Similarity	NPC473562
0.8045	Intermediate Similarity	NPC115906
0.8022	Intermediate Similarity	NPC166979
0.7989	Intermediate Similarity	NPC27887
0.7937	Intermediate Similarity	NPC67346
0.7935	Intermediate Similarity	NPC63152
0.7933	Intermediate Similarity	NPC329816
0.7919	Intermediate Similarity	NPC153631
0.791	Intermediate Similarity	NPC67978
0.791	Intermediate Similarity	NPC303581
0.7904	Intermediate Similarity	NPC214239
0.7898	Intermediate Similarity	NPC86469
0.7874	Intermediate Similarity	NPC476569
0.787	Intermediate Similarity	NPC119669
0.7861	Intermediate Similarity	NPC205167
0.7861	Intermediate Similarity	NPC249274
0.7857	Intermediate Similarity	NPC475566
0.7853	Intermediate Similarity	NPC268077
0.7842	Intermediate Similarity	NPC97086
0.7842	Intermediate Similarity	NPC140577
0.7842	Intermediate Similarity	NPC43069
0.7838	Intermediate Similarity	NPC226708
0.7826	Intermediate Similarity	NPC311339
0.7821	Intermediate Similarity	NPC308267
0.7807	Intermediate Similarity	NPC477258
0.7801	Intermediate Similarity	NPC207971
0.7791	Intermediate Similarity	NPC476443
0.7791	Intermediate Similarity	NPC133817
0.7778	Intermediate Similarity	NPC474470
0.7778	Intermediate Similarity	NPC241704
0.7778	Intermediate Similarity	NPC222524
0.7772	Intermediate Similarity	NPC477259
0.7772	Intermediate Similarity	NPC169387
0.7771	Intermediate Similarity	NPC218614
0.7771	Intermediate Similarity	NPC320104
0.7766	Intermediate Similarity	NPC66909
0.7759	Intermediate Similarity	NPC475780
0.7751	Intermediate Similarity	NPC470088
0.7749	Intermediate Similarity	NPC243483
0.7749	Intermediate Similarity	NPC232533
0.7747	Intermediate Similarity	NPC298339
0.774	Intermediate Similarity	NPC284842
0.774	Intermediate Similarity	NPC190332
0.774	Intermediate Similarity	NPC181653
0.7737	Intermediate Similarity	NPC474427
0.773	Intermediate Similarity	NPC208890
0.7717	Intermediate Similarity	NPC18306
0.7692	Intermediate Similarity	NPC149285
0.7692	Intermediate Similarity	NPC32154
0.7688	Intermediate Similarity	NPC180756
0.7688	Intermediate Similarity	NPC323443
0.7672	Intermediate Similarity	NPC204580
0.7672	Intermediate Similarity	NPC474432
0.7672	Intermediate Similarity	NPC475713
0.7661	Intermediate Similarity	NPC85747
0.7661	Intermediate Similarity	NPC8337
0.766	Intermediate Similarity	NPC469816
0.766	Intermediate Similarity	NPC469815
0.7647	Intermediate Similarity	NPC469539
0.7647	Intermediate Similarity	NPC469540
0.7647	Intermediate Similarity	NPC196231
0.7647	Intermediate Similarity	NPC476436
0.7647	Intermediate Similarity	NPC319549
0.764	Intermediate Similarity	NPC252960
0.764	Intermediate Similarity	NPC100566
0.7637	Intermediate Similarity	NPC121400
0.7632	Intermediate Similarity	NPC83019
0.7632	Intermediate Similarity	NPC71124
0.7619	Intermediate Similarity	NPC469978
0.7619	Intermediate Similarity	NPC470646
0.7604	Intermediate Similarity	NPC151470
0.7604	Intermediate Similarity	NPC201055
0.7604	Intermediate Similarity	NPC64576
0.7604	Intermediate Similarity	NPC254045
0.76	Intermediate Similarity	NPC329640
0.7592	Intermediate Similarity	NPC267414
0.759	Intermediate Similarity	NPC157958
0.7588	Intermediate Similarity	NPC153620
0.7588	Intermediate Similarity	NPC24257
0.7572	Intermediate Similarity	NPC473732
0.7558	Intermediate Similarity	NPC474305
0.7557	Intermediate Similarity	NPC135006
0.7529	Intermediate Similarity	NPC475116
0.7529	Intermediate Similarity	NPC78733
0.7528	Intermediate Similarity	NPC231198
0.7526	Intermediate Similarity	NPC125924
0.7515	Intermediate Similarity	NPC130926
0.7514	Intermediate Similarity	NPC225597
0.7514	Intermediate Similarity	NPC65403
0.7514	Intermediate Similarity	NPC58661
0.7514	Intermediate Similarity	NPC477640
0.7514	Intermediate Similarity	NPC470739
0.7514	Intermediate Similarity	NPC68619
0.7514	Intermediate Similarity	NPC102760
0.75	Intermediate Similarity	NPC326895
0.75	Intermediate Similarity	NPC59028
0.75	Intermediate Similarity	NPC82533
0.75	Intermediate Similarity	NPC158148
0.75	Intermediate Similarity	NPC474306
0.75	Intermediate Similarity	NPC92191
0.75	Intermediate Similarity	NPC290759
0.75	Intermediate Similarity	NPC37065
0.75	Intermediate Similarity	NPC223125
0.75	Intermediate Similarity	NPC475848
0.75	Intermediate Similarity	NPC266176
0.7487	Intermediate Similarity	NPC24228
0.7486	Intermediate Similarity	NPC476002
0.7471	Intermediate Similarity	NPC228662
0.7471	Intermediate Similarity	NPC213900
0.7471	Intermediate Similarity	NPC267091
0.7471	Intermediate Similarity	NPC27106
0.7464	Intermediate Similarity	NPC476429
0.7462	Intermediate Similarity	NPC476495
0.7462	Intermediate Similarity	NPC94687
0.7462	Intermediate Similarity	NPC106840
0.7459	Intermediate Similarity	NPC75958
0.7459	Intermediate Similarity	NPC474953
0.7459	Intermediate Similarity	NPC474475
0.7457	Intermediate Similarity	NPC476579
0.7457	Intermediate Similarity	NPC300983
0.7449	Intermediate Similarity	NPC126211
0.7444	Intermediate Similarity	NPC100420
0.743	Intermediate Similarity	NPC247972
0.7429	Intermediate Similarity	NPC308555
0.7427	Intermediate Similarity	NPC30890
0.7427	Intermediate Similarity	NPC213482
0.7426	Intermediate Similarity	NPC195636
0.7424	Intermediate Similarity	NPC46990
0.7424	Intermediate Similarity	NPC476496
0.7421	Intermediate Similarity	NPC254957
0.7416	Intermediate Similarity	NPC325122
0.7414	Intermediate Similarity	NPC148898
0.7414	Intermediate Similarity	NPC243891
0.7414	Intermediate Similarity	NPC223124
0.7409	Intermediate Similarity	NPC207239
0.7409	Intermediate Similarity	NPC5374
0.7405	Intermediate Similarity	NPC220961
0.7403	Intermediate Similarity	NPC475686
0.7403	Intermediate Similarity	NPC58766
0.7401	Intermediate Similarity	NPC118804
0.7401	Intermediate Similarity	NPC106786
0.7401	Intermediate Similarity	NPC301897
0.7401	Intermediate Similarity	NPC150227
0.7394	Intermediate Similarity	NPC11147
0.7393	Intermediate Similarity	NPC160113
0.7393	Intermediate Similarity	NPC476220
0.7389	Intermediate Similarity	NPC124657
0.7389	Intermediate Similarity	NPC329717
0.7386	Intermediate Similarity	NPC147091
0.7385	Intermediate Similarity	NPC244191
0.7385	Intermediate Similarity	NPC475747
0.7384	Intermediate Similarity	NPC475959
0.7381	Intermediate Similarity	NPC474915
0.7381	Intermediate Similarity	NPC188163
0.7381	Intermediate Similarity	NPC328750
0.7381	Intermediate Similarity	NPC213206
0.738	Intermediate Similarity	NPC116007
0.7376	Intermediate Similarity	NPC38964

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 NPC35680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	621
0.2-0.3	1137
0.3-0.4	2189
0.4-0.5	2512
0.5-0.6	1666
0.6-0.7	735
0.7-0.8	104
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD6386	Approved
0.8424	Intermediate Similarity	NPD6385	Approved
0.8415	Intermediate Similarity	NPD4107	Approved
0.827	Intermediate Similarity	NPD4482	Phase 3
0.8207	Intermediate Similarity	NPD4420	Approved
0.8128	Intermediate Similarity	NPD5006	Approved
0.8128	Intermediate Similarity	NPD5005	Approved
0.8059	Intermediate Similarity	NPD5353	Approved
0.8045	Intermediate Similarity	NPD2968	Approved
0.8045	Intermediate Similarity	NPD2971	Approved
0.8	Intermediate Similarity	NPD4481	Phase 3
0.7966	Intermediate Similarity	NPD5313	Approved
0.7966	Intermediate Similarity	NPD5312	Approved
0.7953	Intermediate Similarity	NPD5977	Approved
0.7953	Intermediate Similarity	NPD5978	Approved
0.7943	Intermediate Similarity	NPD5242	Approved
0.7937	Intermediate Similarity	NPD3057	Approved
0.7842	Intermediate Similarity	NPD2972	Approved
0.7842	Intermediate Similarity	NPD3533	Approved
0.7778	Intermediate Similarity	NPD5980	Discovery
0.7766	Intermediate Similarity	NPD2973	Approved
0.7766	Intermediate Similarity	NPD2974	Approved
0.7766	Intermediate Similarity	NPD2975	Approved
0.7751	Intermediate Similarity	NPD3640	Phase 3
0.7751	Intermediate Similarity	NPD3641	Approved
0.7751	Intermediate Similarity	NPD3639	Approved
0.7749	Intermediate Similarity	NPD3448	Approved
0.7749	Intermediate Similarity	NPD2491	Approved
0.7747	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4580	Approved
0.7727	Intermediate Similarity	NPD6107	Approved
0.7688	Intermediate Similarity	NPD2490	Approved
0.7688	Intermediate Similarity	NPD2488	Approved
0.7674	Intermediate Similarity	NPD6873	Phase 2
0.7647	Intermediate Similarity	NPD7296	Approved
0.7635	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7497	Discontinued
0.7614	Intermediate Similarity	NPD5676	Approved
0.7604	Intermediate Similarity	NPD2493	Approved
0.7604	Intermediate Similarity	NPD3452	Approved
0.7604	Intermediate Similarity	NPD3450	Approved
0.7604	Intermediate Similarity	NPD2494	Approved
0.7577	Intermediate Similarity	NPD4582	Approved
0.7577	Intermediate Similarity	NPD4583	Approved
0.7541	Intermediate Similarity	NPD7038	Approved
0.7541	Intermediate Similarity	NPD7039	Approved
0.7537	Intermediate Similarity	NPD7907	Approved
0.7526	Intermediate Similarity	NPD4004	Approved
0.7526	Intermediate Similarity	NPD4002	Approved
0.7526	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD4111	Phase 1
0.7525	Intermediate Similarity	NPD4665	Approved
0.7514	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4210	Discontinued
0.7471	Intermediate Similarity	NPD7110	Phase 1
0.7471	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2969	Approved
0.7444	Intermediate Similarity	NPD2970	Approved
0.7419	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6875	Approved
0.7414	Intermediate Similarity	NPD6876	Approved
0.7396	Intermediate Similarity	NPD5564	Approved
0.7394	Intermediate Similarity	NPD7291	Discontinued
0.7389	Intermediate Similarity	NPD3051	Approved
0.7381	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2569	Approved
0.7349	Intermediate Similarity	NPD2567	Approved
0.7346	Intermediate Similarity	NPD6625	Approved
0.7345	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2489	Approved
0.7308	Intermediate Similarity	NPD27	Approved
0.7303	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4773	Phase 2
0.7273	Intermediate Similarity	NPD4772	Phase 2
0.7263	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1670	Discontinued
0.7235	Intermediate Similarity	NPD4237	Approved
0.7235	Intermediate Similarity	NPD4236	Phase 3
0.7228	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7177	Discontinued
0.7225	Intermediate Similarity	NPD3146	Approved
0.7225	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4584	Approved
0.7222	Intermediate Similarity	NPD4040	Phase 1
0.7219	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4166	Phase 2
0.7198	Intermediate Similarity	NPD5711	Approved
0.7198	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5773	Approved
0.7191	Intermediate Similarity	NPD5772	Approved
0.7189	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5494	Approved
0.7181	Intermediate Similarity	NPD7313	Approved
0.7181	Intermediate Similarity	NPD7281	Phase 3
0.7181	Intermediate Similarity	NPD7312	Approved
0.7181	Intermediate Similarity	NPD7311	Approved
0.7181	Intermediate Similarity	NPD7310	Approved
0.7181	Intermediate Similarity	NPD7280	Phase 3
0.7169	Intermediate Similarity	NPD3142	Approved
0.7169	Intermediate Similarity	NPD3140	Approved
0.7163	Intermediate Similarity	NPD6997	Phase 2
0.7163	Intermediate Similarity	NPD7048	Phase 3
0.7159	Intermediate Similarity	NPD824	Approved
0.7151	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8285	Discontinued
0.7143	Intermediate Similarity	NPD6851	Approved
0.7143	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD6618	Phase 2
0.7143	Intermediate Similarity	NPD6853	Approved
0.7122	Intermediate Similarity	NPD7047	Phase 3
0.712	Intermediate Similarity	NPD2898	Approved
0.7112	Intermediate Similarity	NPD6297	Approved
0.7104	Intermediate Similarity	NPD7315	Approved
0.7072	Intermediate Similarity	NPD1307	Phase 2
0.7072	Intermediate Similarity	NPD1309	Phase 2
0.7062	Intermediate Similarity	NPD3455	Phase 2
0.7056	Intermediate Similarity	NPD2560	Approved
0.7056	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2563	Approved
0.7056	Intermediate Similarity	NPD7565	Approved
0.7052	Intermediate Similarity	NPD5241	Discontinued
0.7045	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2163	Approved
0.7035	Intermediate Similarity	NPD2654	Approved
0.7031	Intermediate Similarity	NPD7906	Approved
0.7015	Intermediate Similarity	NPD7999	Approved
0.7015	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6071	Discontinued
0.7006	Intermediate Similarity	NPD3687	Approved
0.7006	Intermediate Similarity	NPD3686	Approved
0.7005	Intermediate Similarity	NPD8404	Phase 2
0.7005	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4585	Approved
0.7	Intermediate Similarity	NPD4577	Approved
0.7	Intermediate Similarity	NPD4578	Approved
0.7	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5754	Discontinued
0.6983	Remote Similarity	NPD4424	Discontinued
0.6982	Remote Similarity	NPD2653	Approved
0.6979	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4663	Approved
0.6976	Remote Similarity	NPD7827	Phase 1
0.6971	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.695	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7427	Discontinued
0.6946	Remote Similarity	NPD4859	Phase 1
0.6944	Remote Similarity	NPD37	Approved
0.6944	Remote Similarity	NPD7298	Approved
0.6941	Remote Similarity	NPD743	Approved
0.6941	Remote Similarity	NPD5688	Approved
0.6941	Remote Similarity	NPD5689	Approved
0.6939	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3823	Discontinued
0.6928	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6923	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8156	Discontinued
0.6914	Remote Similarity	NPD6666	Approved
0.6914	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6667	Approved
0.6906	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2492	Phase 1
0.6878	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5297	Approved
0.6872	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4017	Approved
0.6872	Remote Similarity	NPD2649	Approved
0.6872	Remote Similarity	NPD2651	Approved
0.6862	Remote Similarity	NPD8099	Discontinued
0.6862	Remote Similarity	NPD8251	Approved
0.6862	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8252	Approved
0.6859	Remote Similarity	NPD7549	Discontinued
0.6857	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6031	Approved
0.6854	Remote Similarity	NPD6030	Approved
0.6851	Remote Similarity	NPD7577	Discontinued
0.6851	Remote Similarity	NPD6844	Discontinued
0.6848	Remote Similarity	NPD6234	Discontinued
0.6845	Remote Similarity	NPD5718	Phase 2
0.6842	Remote Similarity	NPD6895	Approved
0.6842	Remote Similarity	NPD6896	Approved
0.6839	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5071	Phase 2

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