NPASS Compound

Structure

NPC226862 OpenBabel07101719522D 26 29 0 0 1 0 0 0 0 0999 V2000 0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0540 0.5885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8283 -2.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2514 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0505 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6527 -0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2460 -1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6472 -0.3250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8337 -2.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4627 1.4023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4627 -0.2158 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 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 14 1 1 0 0 0 20 26 1 0 0 0 0 21 15 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	365.679
LogP:	4.646
LogD:	3.941
LogS:	-5.713
# Rotatable Bonds:	4
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	3.369
Fsp3:	0.429
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:	-4.798
MDCK Permeability:	7.793374243192375e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	95.17527770996094%
Volume Distribution (VD):	1.526
Pgp-substrate:	1.6504042148590088%

ADMET: Metabolism

CYP1A2-inhibitor:	0.414
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.916
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.754

ADMET: Excretion

Clearance (CL):	15.574
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.134
Skin Sensitization:	0.612
Carcinogencity:	0.807
Eye Corrosion:	0.004
Eye Irritation:	0.237
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC226862

Natural Product ID:	NPC226862
*Common Name:**	Calopiptin
IUPAC Name:	5-[(2S,3S,4S,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-1,3-benzodioxole
Synonyms:	Calopiptin
Standard InCHIKey:	HSMDOSKNXLVXIP-IRTBSJMASA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-12-13(2)21(15-6-8-17-19(10-15)25-11-24-17)26-20(12)14-5-7-16(22-3)18(9-14)23-4/h5-10,12-13,20-21H,11H2,1-4H3/t12-,13-,20+,21-/m0/s1
SMILES:	C[C@H]1[C@H](C)[C@@H](c2ccc3c(c2)OCO3)O[C@H]1c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469499
PubChem CID:	12302265
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO3739	Nectandra megapotamica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738383]
NPO3739	Nectandra megapotamica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15324487]
NPO3739	Nectandra megapotamica	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[26184150]
NPO3739	Nectandra megapotamica	Species	Lauraceae	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	1
Others	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	21.4	%	PMID[534103]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	49.2	%	PMID[534103]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	60.3	%	PMID[534103]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	12600.0	nM	PMID[534103]

☑ 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 NPC226862 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	452
0.1-0.2	1454
0.2-0.3	3783
0.3-0.4	11060
0.4-0.5	8045
0.5-0.6	6685
0.6-0.7	8240
0.7-0.8	2348
0.8-0.85	401
0.85-0.9	164
0.9-0.95	53
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158471
1.0	High Similarity	NPC57119
1.0	High Similarity	NPC165128
0.9837	High Similarity	NPC233224
0.9837	High Similarity	NPC271208
0.9758	High Similarity	NPC82111
0.9758	High Similarity	NPC227160
0.968	High Similarity	NPC7744
0.9603	High Similarity	NPC136750
0.9603	High Similarity	NPC266848
0.9528	High Similarity	NPC90083
0.9528	High Similarity	NPC170779
0.9524	High Similarity	NPC16830
0.9524	High Similarity	NPC158526
0.9524	High Similarity	NPC72046
0.9524	High Similarity	NPC129687
0.9524	High Similarity	NPC147616
0.9524	High Similarity	NPC33611
0.9524	High Similarity	NPC259742
0.9524	High Similarity	NPC104077
0.9524	High Similarity	NPC219671
0.9524	High Similarity	NPC100223
0.9524	High Similarity	NPC261812
0.9524	High Similarity	NPC65183
0.9524	High Similarity	NPC171928
0.9508	High Similarity	NPC34902
0.9508	High Similarity	NPC18449
0.9508	High Similarity	NPC121783
0.9453	High Similarity	NPC189474
0.9453	High Similarity	NPC135777
0.9453	High Similarity	NPC474139
0.9453	High Similarity	NPC142547
0.9444	High Similarity	NPC192255
0.9435	High Similarity	NPC158737
0.9421	High Similarity	NPC126935
0.9421	High Similarity	NPC312713
0.9421	High Similarity	NPC65933
0.9421	High Similarity	NPC216929
0.9421	High Similarity	NPC57268
0.9421	High Similarity	NPC301641
0.9421	High Similarity	NPC172676
0.9421	High Similarity	NPC80241
0.9375	High Similarity	NPC31530
0.9375	High Similarity	NPC47181
0.9302	High Similarity	NPC148893
0.9302	High Similarity	NPC18576
0.9302	High Similarity	NPC49235
0.9302	High Similarity	NPC25333
0.9286	High Similarity	NPC476748
0.9256	High Similarity	NPC344161
0.9237	High Similarity	NPC123526
0.9237	High Similarity	NPC193666
0.9237	High Similarity	NPC88640
0.9231	High Similarity	NPC121651
0.9219	High Similarity	NPC471505
0.9206	High Similarity	NPC222127
0.9206	High Similarity	NPC82862
0.92	High Similarity	NPC213711
0.92	High Similarity	NPC40352
0.916	High Similarity	NPC101807
0.916	High Similarity	NPC469981
0.916	High Similarity	NPC185908
0.9154	High Similarity	NPC174191
0.9127	High Similarity	NPC473093
0.9127	High Similarity	NPC473092
0.9127	High Similarity	NPC8050
0.9098	High Similarity	NPC312199
0.9091	High Similarity	NPC156376
0.9091	High Similarity	NPC113550
0.9084	High Similarity	NPC11453
0.907	High Similarity	NPC106739
0.9062	High Similarity	NPC171550
0.9062	High Similarity	NPC134764
0.9055	High Similarity	NPC281864
0.9055	High Similarity	NPC54321
0.9055	High Similarity	NPC328682
0.9048	High Similarity	NPC206882
0.9048	High Similarity	NPC285725
0.9048	High Similarity	NPC112571
0.9048	High Similarity	NPC50683
0.903	High Similarity	NPC80326
0.903	High Similarity	NPC472562
0.903	High Similarity	NPC302506
0.903	High Similarity	NPC246947
0.9023	High Similarity	NPC177868
0.9023	High Similarity	NPC216434
0.9023	High Similarity	NPC46591
0.9023	High Similarity	NPC103448
0.9015	High Similarity	NPC283949
0.9015	High Similarity	NPC166184
0.9008	High Similarity	NPC150534
0.9008	High Similarity	NPC101624
0.9008	High Similarity	NPC184938
0.9	High Similarity	NPC196937
0.9	High Similarity	NPC1474
0.9	High Similarity	NPC169973
0.8992	High Similarity	NPC27843
0.8992	High Similarity	NPC40432
0.8992	High Similarity	NPC115207
0.8992	High Similarity	NPC161557
0.8992	High Similarity	NPC228346
0.8992	High Similarity	NPC7171
0.8992	High Similarity	NPC158079
0.8976	High Similarity	NPC177167
0.8976	High Similarity	NPC98745
0.8963	High Similarity	NPC255566
0.8963	High Similarity	NPC298317
0.8963	High Similarity	NPC265154
0.8963	High Similarity	NPC477898
0.8955	High Similarity	NPC300798
0.8955	High Similarity	NPC471908
0.8955	High Similarity	NPC58137
0.8939	High Similarity	NPC143895
0.8923	High Similarity	NPC181049
0.8923	High Similarity	NPC207400
0.8915	High Similarity	NPC275950
0.8906	High Similarity	NPC184733
0.8906	High Similarity	NPC45774
0.8906	High Similarity	NPC11258
0.8906	High Similarity	NPC21867
0.8906	High Similarity	NPC129570
0.8906	High Similarity	NPC282703
0.8906	High Similarity	NPC470084
0.8906	High Similarity	NPC128208
0.8898	High Similarity	NPC9891
0.8898	High Similarity	NPC186845
0.8898	High Similarity	NPC88297
0.8897	High Similarity	NPC179521
0.8897	High Similarity	NPC84181
0.8889	High Similarity	NPC287124
0.8889	High Similarity	NPC311057
0.8889	High Similarity	NPC474295
0.8889	High Similarity	NPC174522
0.8881	High Similarity	NPC226547
0.8881	High Similarity	NPC56091
0.8881	High Similarity	NPC278076
0.8855	High Similarity	NPC205915
0.8846	High Similarity	NPC476345
0.8832	High Similarity	NPC180953
0.8832	High Similarity	NPC22150
0.8832	High Similarity	NPC279298
0.8832	High Similarity	NPC38041
0.8824	High Similarity	NPC474808
0.8824	High Similarity	NPC12728
0.8824	High Similarity	NPC185071
0.8819	High Similarity	NPC17348
0.8815	High Similarity	NPC472711
0.881	High Similarity	NPC249788
0.8797	High Similarity	NPC32189
0.8779	High Similarity	NPC4940
0.8779	High Similarity	NPC97316
0.877	High Similarity	NPC81067
0.877	High Similarity	NPC9341
0.8769	High Similarity	NPC174495
0.8769	High Similarity	NPC77040
0.8769	High Similarity	NPC92164
0.8769	High Similarity	NPC173308
0.8769	High Similarity	NPC257582
0.8769	High Similarity	NPC64201
0.8769	High Similarity	NPC181079
0.8769	High Similarity	NPC153739
0.8769	High Similarity	NPC145305
0.8769	High Similarity	NPC187998
0.8769	High Similarity	NPC242807
0.8769	High Similarity	NPC241522
0.8769	High Similarity	NPC42300
0.8768	High Similarity	NPC112861
0.8768	High Similarity	NPC205796
0.8768	High Similarity	NPC276753
0.8768	High Similarity	NPC93610
0.8768	High Similarity	NPC241846
0.8759	High Similarity	NPC166884
0.8759	High Similarity	NPC141569
0.8759	High Similarity	NPC477701
0.875	High Similarity	NPC274356
0.875	High Similarity	NPC210354
0.875	High Similarity	NPC176586
0.8731	High Similarity	NPC196420
0.8731	High Similarity	NPC474039
0.8722	High Similarity	NPC236522
0.8722	High Similarity	NPC126409
0.8722	High Similarity	NPC99572
0.8702	High Similarity	NPC277804
0.8696	High Similarity	NPC477702
0.8696	High Similarity	NPC205316
0.8696	High Similarity	NPC18979
0.8692	High Similarity	NPC475875
0.8686	High Similarity	NPC185307
0.8686	High Similarity	NPC470950
0.8678	High Similarity	NPC165106
0.8667	High Similarity	NPC9068
0.8661	High Similarity	NPC279379
0.8657	High Similarity	NPC78047
0.8657	High Similarity	NPC25695
0.8657	High Similarity	NPC172818
0.8647	High Similarity	NPC256776
0.8647	High Similarity	NPC110958
0.8647	High Similarity	NPC67247
0.8647	High Similarity	NPC145722
0.8647	High Similarity	NPC19890

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 NPC226862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	863
0.2-0.3	1610
0.3-0.4	2856
0.4-0.5	1833
0.5-0.6	1064
0.6-0.7	501
0.7-0.8	77
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
0.9106	High Similarity	NPD3705	Approved
0.8678	High Similarity	NPD5283	Phase 1
0.8134	Intermediate Similarity	NPD3027	Phase 3
0.8125	Intermediate Similarity	NPD1357	Approved
0.8054	Intermediate Similarity	NPD4965	Approved
0.8054	Intermediate Similarity	NPD4967	Phase 2
0.8054	Intermediate Similarity	NPD4966	Approved
0.8042	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6234	Discontinued
0.7852	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD6674	Discontinued
0.7746	Intermediate Similarity	NPD1375	Discontinued
0.7744	Intermediate Similarity	NPD2981	Phase 2
0.7721	Intermediate Similarity	NPD2861	Phase 2
0.7692	Intermediate Similarity	NPD5536	Phase 2
0.7687	Intermediate Similarity	NPD2982	Phase 2
0.7687	Intermediate Similarity	NPD2983	Phase 2
0.7635	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7199	Phase 2
0.7603	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7228	Approved
0.7591	Intermediate Similarity	NPD3018	Phase 2
0.7571	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1613	Approved
0.7554	Intermediate Similarity	NPD5109	Approved
0.7554	Intermediate Similarity	NPD5111	Phase 2
0.7554	Intermediate Similarity	NPD5110	Phase 2
0.7534	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3657	Discovery
0.7517	Intermediate Similarity	NPD4237	Approved
0.7517	Intermediate Similarity	NPD4236	Phase 3
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD228	Approved
0.7483	Intermediate Similarity	NPD5058	Phase 3
0.7467	Intermediate Similarity	NPD4210	Discontinued
0.7466	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4110	Phase 3
0.7451	Intermediate Similarity	NPD2978	Approved
0.7451	Intermediate Similarity	NPD2977	Approved
0.7447	Intermediate Similarity	NPD3620	Phase 2
0.7447	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5327	Phase 3
0.741	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7240	Approved
0.7407	Intermediate Similarity	NPD1091	Approved
0.7405	Intermediate Similarity	NPD7157	Approved
0.7402	Intermediate Similarity	NPD2684	Approved
0.7368	Intermediate Similarity	NPD7028	Phase 2
0.7361	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4108	Discontinued
0.7361	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6331	Phase 2
0.7344	Intermediate Similarity	NPD3021	Approved
0.7344	Intermediate Similarity	NPD3022	Approved
0.7338	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4060	Phase 1
0.7313	Intermediate Similarity	NPD5585	Approved
0.731	Intermediate Similarity	NPD2161	Phase 2
0.7308	Intermediate Similarity	NPD5535	Approved
0.7308	Intermediate Similarity	NPD7843	Approved
0.7303	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6895	Approved
0.7292	Intermediate Similarity	NPD6896	Approved
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7259	Intermediate Similarity	NPD5126	Approved
0.7259	Intermediate Similarity	NPD5125	Phase 3
0.7259	Intermediate Similarity	NPD17	Approved
0.7254	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7124	Phase 2
0.723	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5494	Approved
0.7209	Intermediate Similarity	NPD5451	Approved
0.7203	Intermediate Similarity	NPD2979	Phase 3
0.7197	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2438	Suspended
0.7188	Intermediate Similarity	NPD1358	Approved
0.7185	Intermediate Similarity	NPD5691	Approved
0.7183	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3060	Approved
0.7161	Intermediate Similarity	NPD3382	Approved
0.7161	Intermediate Similarity	NPD3383	Approved
0.7161	Intermediate Similarity	NPD3384	Approved
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7153	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD6387	Discontinued
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1653	Approved
0.7123	Intermediate Similarity	NPD5588	Approved
0.7122	Intermediate Similarity	NPD8651	Approved
0.7122	Intermediate Similarity	NPD2922	Phase 1
0.7113	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD1182	Approved
0.7109	Intermediate Similarity	NPD3134	Approved
0.7105	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2492	Phase 1
0.7101	Intermediate Similarity	NPD1608	Approved
0.7101	Intermediate Similarity	NPD1840	Phase 2
0.7099	Intermediate Similarity	NPD1139	Approved
0.7099	Intermediate Similarity	NPD1137	Approved
0.7083	Intermediate Similarity	NPD1558	Phase 1
0.7083	Intermediate Similarity	NPD4140	Approved
0.7075	Intermediate Similarity	NPD3539	Phase 1
0.707	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5718	Phase 2
0.7059	Intermediate Similarity	NPD1651	Approved
0.7059	Intermediate Similarity	NPD5976	Discontinued
0.7055	Intermediate Similarity	NPD4538	Approved
0.7055	Intermediate Similarity	NPD6111	Discontinued
0.7055	Intermediate Similarity	NPD4536	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7055	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4359	Approved
0.705	Intermediate Similarity	NPD3685	Discontinued
0.7047	Intermediate Similarity	NPD4162	Approved
0.7045	Intermediate Similarity	NPD1138	Approved
0.7039	Intermediate Similarity	NPD4123	Phase 3
0.7029	Intermediate Similarity	NPD1281	Approved
0.7027	Intermediate Similarity	NPD3540	Phase 1
0.7015	Intermediate Similarity	NPD709	Approved
0.7007	Intermediate Similarity	NPD5846	Approved
0.7007	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6993	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7685	Pre-registration
0.6987	Remote Similarity	NPD6385	Approved
0.6987	Remote Similarity	NPD6386	Approved
0.6986	Remote Similarity	NPD6353	Approved
0.6981	Remote Similarity	NPD5604	Discontinued
0.698	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7074	Phase 3
0.6966	Remote Similarity	NPD2238	Phase 2
0.6963	Remote Similarity	NPD3596	Phase 2
0.6957	Remote Similarity	NPD8127	Discontinued
0.6954	Remote Similarity	NPD2677	Approved
0.6944	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD1934	Approved
0.6939	Remote Similarity	NPD7119	Phase 2
0.6933	Remote Similarity	NPD5177	Phase 3
0.6933	Remote Similarity	NPD4481	Phase 3
0.6913	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7054	Approved
0.6906	Remote Similarity	NPD1611	Approved
0.6905	Remote Similarity	NPD3020	Approved
0.6903	Remote Similarity	NPD3686	Approved
0.6903	Remote Similarity	NPD3687	Approved
0.6901	Remote Similarity	NPD4624	Approved
0.6901	Remote Similarity	NPD6584	Phase 3
0.6899	Remote Similarity	NPD5772	Approved
0.6899	Remote Similarity	NPD5773	Approved
0.6899	Remote Similarity	NPD8455	Phase 2
0.6897	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD4870	Approved
0.6892	Remote Similarity	NPD5960	Phase 3
0.6889	Remote Similarity	NPD6671	Approved
0.6884	Remote Similarity	NPD2667	Approved
0.6884	Remote Similarity	NPD2668	Approved
0.6884	Remote Similarity	NPD4626	Approved
0.6883	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7526	Approved
0.6883	Remote Similarity	NPD52	Approved
0.6879	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6653	Approved
0.6871	Remote Similarity	NPD2653	Approved
0.6867	Remote Similarity	NPD7472	Approved
0.6867	Remote Similarity	NPD2808	Discontinued
0.6861	Remote Similarity	NPD6581	Approved
0.6861	Remote Similarity	NPD6580	Approved
0.6861	Remote Similarity	NPD1548	Phase 1
0.6859	Remote Similarity	NPD4005	Discontinued
0.6857	Remote Similarity	NPD2233	Approved
0.6857	Remote Similarity	NPD2231	Phase 2
0.6857	Remote Similarity	NPD2235	Phase 2
0.6857	Remote Similarity	NPD2232	Approved
0.6857	Remote Similarity	NPD2230	Approved
0.6855	Remote Similarity	NPD2563	Approved
0.6855	Remote Similarity	NPD3817	Phase 2
0.6855	Remote Similarity	NPD2560	Approved
0.6855	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2531	Phase 2
0.6846	Remote Similarity	NPD968	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