NPASS Compound

Structure

CID205915 OpenBabel06191715592D 27 30 0 0 1 0 0 0 0 0999 V2000 4.0428 -5.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3975 -5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 -3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 -2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6369 -3.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8838 -4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9328 -3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0917 -5.1727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 -4.5546 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 -3.0491 -4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 -2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 12 27 1 0 0 0 0 15 7 1 6 0 0 0 15 16 1 0 0 0 0 16 8 1 1 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	371.832
LogP:	3.347
LogD:	3.275
LogS:	-5.228
# Rotatable Bonds:	6
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	3.1
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.881
MDCK Permeability:	2.9192640795372427e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	97.3163070678711%
Volume Distribution (VD):	0.962
Pgp-substrate:	2.8893215656280518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.979
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	14.295
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.816
Carcinogencity:	0.767
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.552

Download Data

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

Natural Product: NPC205915

Natural Product ID:	NPC205915
*Common Name:**	(-)-Kusunokinin
IUPAC Name:	(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
Synonyms:
Standard InCHIKey:	LEVKKQBBEVGIKN-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3/t15-,16+/m0/s1
SMILES:	COc1ccc(C[C@H]2COC(=O)[C@@H]2Cc2ccc3c(c2)OCO3)cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228191
PubChem CID:	384876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	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	2
LD50	1
Others	1

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1516	Organism	Anticarsia gemmatalis	Anticarsia gemmatalis	LD50	=	230.1	ug/uL	PMID[462968]
NPT1516	Organism	Anticarsia gemmatalis	Anticarsia gemmatalis	LD10	=	9.3	ug/uL	PMID[462968]
NPT2	Others	Unspecified		IC50	=	8200.0	nM	PMID[462969]
NPT2	Others	Unspecified		IC50	=	2700.0	nM	PMID[462969]

☑ 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 NPC205915 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	317
0.1-0.2	1378
0.2-0.3	2910
0.3-0.4	8511
0.4-0.5	10994
0.5-0.6	5116
0.6-0.7	11230
0.7-0.8	1908
0.8-0.85	220
0.85-0.9	89
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9766	High Similarity	NPC19890
0.9766	High Similarity	NPC110958
0.9524	High Similarity	NPC223807
0.9474	High Similarity	NPC166137
0.9474	High Similarity	NPC282291
0.9466	High Similarity	NPC230968
0.9466	High Similarity	NPC102260
0.9403	High Similarity	NPC176586
0.9403	High Similarity	NPC210354
0.9375	High Similarity	NPC476748
0.9328	High Similarity	NPC246474
0.9328	High Similarity	NPC162851
0.9328	High Similarity	NPC218092
0.9265	High Similarity	NPC191158
0.9265	High Similarity	NPC177644
0.9259	High Similarity	NPC40237
0.9259	High Similarity	NPC151423
0.9124	High Similarity	NPC218841
0.9124	High Similarity	NPC92693
0.9124	High Similarity	NPC475000
0.9051	High Similarity	NPC474288
0.9048	High Similarity	NPC80241
0.9048	High Similarity	NPC301641
0.9023	High Similarity	NPC4982
0.9023	High Similarity	NPC68779
0.9023	High Similarity	NPC300776
0.9023	High Similarity	NPC5310
0.9023	High Similarity	NPC176814
0.8993	High Similarity	NPC3982
0.8993	High Similarity	NPC193779
0.8978	High Similarity	NPC52664
0.8955	High Similarity	NPC211386
0.8936	High Similarity	NPC145569
0.8936	High Similarity	NPC216223
0.8929	High Similarity	NPC304687
0.8929	High Similarity	NPC104024
0.8929	High Similarity	NPC65574
0.8929	High Similarity	NPC80230
0.8929	High Similarity	NPC101755
0.8923	High Similarity	NPC158737
0.8889	High Similarity	NPC344161
0.8855	High Similarity	NPC165128
0.8855	High Similarity	NPC57119
0.8855	High Similarity	NPC158471
0.8855	High Similarity	NPC226862
0.8824	High Similarity	NPC14022
0.8815	High Similarity	NPC44245
0.8815	High Similarity	NPC72796
0.8803	High Similarity	NPC177476
0.8803	High Similarity	NPC477695
0.8803	High Similarity	NPC262455
0.8803	High Similarity	NPC668
0.8803	High Similarity	NPC127827
0.8803	High Similarity	NPC174512
0.8803	High Similarity	NPC474965
0.8803	High Similarity	NPC477698
0.8803	High Similarity	NPC293757
0.8786	High Similarity	NPC474158
0.875	High Similarity	NPC11453
0.875	High Similarity	NPC56184
0.875	High Similarity	NPC90431
0.8741	High Similarity	NPC149505
0.8741	High Similarity	NPC475722
0.8722	High Similarity	NPC233224
0.8722	High Similarity	NPC271208
0.8714	High Similarity	NPC474036
0.8714	High Similarity	NPC15743
0.8702	High Similarity	NPC40352
0.8702	High Similarity	NPC213711
0.869	High Similarity	NPC308555
0.8686	High Similarity	NPC52968
0.8686	High Similarity	NPC231719
0.8681	High Similarity	NPC210642
0.8681	High Similarity	NPC303519
0.8681	High Similarity	NPC13985
0.8681	High Similarity	NPC164082
0.8681	High Similarity	NPC477700
0.8662	High Similarity	NPC153620
0.8662	High Similarity	NPC24257
0.8657	High Similarity	NPC227160
0.8657	High Similarity	NPC192255
0.8657	High Similarity	NPC82111
0.8652	High Similarity	NPC223185
0.8636	High Similarity	NPC64948
0.8636	High Similarity	NPC177167
0.8633	High Similarity	NPC29599
0.8633	High Similarity	NPC100675
0.8626	High Similarity	NPC85830
0.8621	High Similarity	NPC477699
0.8613	High Similarity	NPC143895
0.8611	High Similarity	NPC229882
0.8611	High Similarity	NPC158635
0.8605	High Similarity	NPC114845
0.8601	High Similarity	NPC181464
0.8601	High Similarity	NPC262804
0.8601	High Similarity	NPC40654
0.8593	High Similarity	NPC7744
0.8582	High Similarity	NPC171550
0.8582	High Similarity	NPC134764
0.8571	High Similarity	NPC186316
0.8571	High Similarity	NPC253722
0.8571	High Similarity	NPC31751
0.8571	High Similarity	NPC254163
0.8571	High Similarity	NPC253481
0.8552	High Similarity	NPC32079
0.8552	High Similarity	NPC474975
0.8551	High Similarity	NPC166184
0.8542	High Similarity	NPC24193
0.854	High Similarity	NPC113295
0.8529	High Similarity	NPC169973
0.8529	High Similarity	NPC136750
0.8529	High Similarity	NPC266848
0.8521	High Similarity	NPC327052
0.8514	High Similarity	NPC478055
0.8511	High Similarity	NPC86455
0.8511	High Similarity	NPC106920
0.8511	High Similarity	NPC472564
0.8511	High Similarity	NPC273657
0.8511	High Similarity	NPC137920
0.8511	High Similarity	NPC125134
0.8503	High Similarity	NPC348849
0.8503	High Similarity	NPC273578
0.8503	High Similarity	NPC178195
0.8503	High Similarity	NPC136757
0.8503	High Similarity	NPC30009
0.8503	High Similarity	NPC103197
0.85	High Similarity	NPC323601
0.85	High Similarity	NPC28398
0.85	High Similarity	NPC51681
0.8485	Intermediate Similarity	NPC17348
0.8478	Intermediate Similarity	NPC209229
0.8473	Intermediate Similarity	NPC249788
0.8473	Intermediate Similarity	NPC470887
0.8467	Intermediate Similarity	NPC90083
0.8467	Intermediate Similarity	NPC170779
0.8467	Intermediate Similarity	NPC37065
0.8456	Intermediate Similarity	NPC72046
0.8456	Intermediate Similarity	NPC129687
0.8456	Intermediate Similarity	NPC158526
0.8456	Intermediate Similarity	NPC104077
0.8456	Intermediate Similarity	NPC171928
0.8456	Intermediate Similarity	NPC259742
0.8456	Intermediate Similarity	NPC100223
0.8456	Intermediate Similarity	NPC219671
0.8456	Intermediate Similarity	NPC65183
0.8456	Intermediate Similarity	NPC261812
0.8456	Intermediate Similarity	NPC33611
0.8456	Intermediate Similarity	NPC147616
0.8456	Intermediate Similarity	NPC16830
0.8451	Intermediate Similarity	NPC46880
0.8444	Intermediate Similarity	NPC477694
0.8444	Intermediate Similarity	NPC477705
0.8444	Intermediate Similarity	NPC275950
0.844	Intermediate Similarity	NPC287124
0.8435	Intermediate Similarity	NPC245615
0.8435	Intermediate Similarity	NPC299706
0.8435	Intermediate Similarity	NPC115466
0.8435	Intermediate Similarity	NPC61604
0.8421	Intermediate Similarity	NPC274356
0.8409	Intermediate Similarity	NPC121783
0.8409	Intermediate Similarity	NPC34902
0.8409	Intermediate Similarity	NPC18449
0.8406	Intermediate Similarity	NPC189474
0.8406	Intermediate Similarity	NPC474139
0.8406	Intermediate Similarity	NPC135777
0.8406	Intermediate Similarity	NPC142547
0.8403	Intermediate Similarity	NPC25496
0.8389	Intermediate Similarity	NPC239113
0.8389	Intermediate Similarity	NPC32373
0.8389	Intermediate Similarity	NPC261484
0.8389	Intermediate Similarity	NPC115123
0.8389	Intermediate Similarity	NPC237946
0.8382	Intermediate Similarity	NPC477706
0.8382	Intermediate Similarity	NPC476345
0.838	Intermediate Similarity	NPC477696
0.838	Intermediate Similarity	NPC477697
0.838	Intermediate Similarity	NPC470811
0.8372	Intermediate Similarity	NPC69670
0.837	Intermediate Similarity	NPC241354
0.8357	Intermediate Similarity	NPC178290
0.8346	Intermediate Similarity	NPC280767
0.8344	Intermediate Similarity	NPC96593
0.8344	Intermediate Similarity	NPC470637
0.8333	Intermediate Similarity	NPC115281
0.8333	Intermediate Similarity	NPC31530
0.8333	Intermediate Similarity	NPC165106
0.8333	Intermediate Similarity	NPC163527
0.8333	Intermediate Similarity	NPC19947
0.8333	Intermediate Similarity	NPC207584
0.8333	Intermediate Similarity	NPC47181
0.8333	Intermediate Similarity	NPC181168
0.8322	Intermediate Similarity	NPC141569
0.8322	Intermediate Similarity	NPC18211
0.8322	Intermediate Similarity	NPC38699
0.8322	Intermediate Similarity	NPC234730
0.8322	Intermediate Similarity	NPC477701
0.8322	Intermediate Similarity	NPC166884
0.8321	Intermediate Similarity	NPC126935
0.8321	Intermediate Similarity	NPC312713
0.8321	Intermediate Similarity	NPC216929

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 NPC205915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	863
0.2-0.3	1406
0.3-0.4	2587
0.4-0.5	2152
0.5-0.6	1206
0.6-0.7	578
0.7-0.8	81
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8521	High Similarity	NPD6143	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD4967	Phase 2
0.8389	Intermediate Similarity	NPD4966	Approved
0.8389	Intermediate Similarity	NPD4965	Approved
0.8333	Intermediate Similarity	NPD5283	Phase 1
0.8278	Intermediate Similarity	NPD6234	Discontinued
0.8188	Intermediate Similarity	NPD37	Approved
0.8182	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4110	Phase 3
0.8182	Intermediate Similarity	NPD3705	Approved
0.8095	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD6355	Discontinued
0.7949	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5536	Phase 2
0.7933	Intermediate Similarity	NPD7028	Phase 2
0.7929	Intermediate Similarity	NPD2979	Phase 3
0.7911	Intermediate Similarity	NPD7228	Approved
0.791	Intermediate Similarity	NPD1281	Approved
0.7902	Intermediate Similarity	NPD2438	Suspended
0.782	Intermediate Similarity	NPD5585	Approved
0.7761	Intermediate Similarity	NPD17	Approved
0.7737	Intermediate Similarity	NPD1283	Approved
0.7716	Intermediate Similarity	NPD7240	Approved
0.7687	Intermediate Similarity	NPD1651	Approved
0.7687	Intermediate Similarity	NPD1357	Approved
0.7662	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6798	Discontinued
0.7655	Intermediate Similarity	NPD2531	Phase 2
0.7622	Intermediate Similarity	NPD1933	Approved
0.7606	Intermediate Similarity	NPD8032	Phase 2
0.7591	Intermediate Similarity	NPD1608	Approved
0.7589	Intermediate Similarity	NPD7095	Approved
0.7576	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5535	Approved
0.7552	Intermediate Similarity	NPD4060	Phase 1
0.7536	Intermediate Similarity	NPD4359	Approved
0.7536	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4062	Phase 3
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.7481	Intermediate Similarity	NPD1894	Discontinued
0.7445	Intermediate Similarity	NPD3847	Discontinued
0.7442	Intermediate Similarity	NPD1358	Approved
0.7432	Intermediate Similarity	NPD5958	Discontinued
0.7426	Intermediate Similarity	NPD5691	Approved
0.7425	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6386	Approved
0.7419	Intermediate Similarity	NPD6873	Phase 2
0.7419	Intermediate Similarity	NPD6385	Approved
0.741	Intermediate Similarity	NPD7281	Phase 3
0.741	Intermediate Similarity	NPD7280	Phase 3
0.7403	Intermediate Similarity	NPD7458	Discontinued
0.7397	Intermediate Similarity	NPD7097	Phase 1
0.7364	Intermediate Similarity	NPD3134	Approved
0.7357	Intermediate Similarity	NPD1876	Approved
0.7347	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7315	Intermediate Similarity	NPD4534	Discontinued
0.7312	Intermediate Similarity	NPD5494	Approved
0.7305	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD5110	Phase 2
0.7292	Intermediate Similarity	NPD5109	Approved
0.7292	Intermediate Similarity	NPD5111	Phase 2
0.7292	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD8127	Discontinued
0.726	Intermediate Similarity	NPD4622	Approved
0.726	Intermediate Similarity	NPD4618	Approved
0.7256	Intermediate Similarity	NPD3818	Discontinued
0.7255	Intermediate Similarity	NPD3146	Approved
0.7255	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5647	Approved
0.7254	Intermediate Similarity	NPD2798	Approved
0.7241	Intermediate Similarity	NPD4870	Approved
0.7239	Intermediate Similarity	NPD1241	Discontinued
0.7237	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD8166	Discontinued
0.7218	Intermediate Similarity	NPD228	Approved
0.7214	Intermediate Similarity	NPD3972	Approved
0.7211	Intermediate Similarity	NPD6653	Approved
0.7211	Intermediate Similarity	NPD2653	Approved
0.7208	Intermediate Similarity	NPD6273	Approved
0.7203	Intermediate Similarity	NPD9494	Approved
0.7192	Intermediate Similarity	NPD4140	Approved
0.7181	Intermediate Similarity	NPD6032	Approved
0.7181	Intermediate Similarity	NPD4476	Approved
0.7181	Intermediate Similarity	NPD4477	Approved
0.7181	Intermediate Similarity	NPD2935	Discontinued
0.7178	Intermediate Similarity	NPD5242	Approved
0.7172	Intermediate Similarity	NPD3268	Approved
0.717	Intermediate Similarity	NPD3817	Phase 2
0.7162	Intermediate Similarity	NPD5688	Approved
0.7162	Intermediate Similarity	NPD5689	Approved
0.7153	Intermediate Similarity	NPD2614	Approved
0.7153	Intermediate Similarity	NPD6832	Phase 2
0.7153	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3657	Discovery
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7132	Intermediate Similarity	NPD7157	Approved
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7123	Intermediate Similarity	NPD6663	Approved
0.7122	Intermediate Similarity	NPD4626	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7114	Intermediate Similarity	NPD4108	Discontinued
0.7114	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8455	Phase 2
0.7102	Intermediate Similarity	NPD4420	Approved
0.7095	Intermediate Similarity	NPD2492	Phase 1
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.7092	Intermediate Similarity	NPD2981	Phase 2
0.7086	Intermediate Similarity	NPD2897	Discontinued
0.7075	Intermediate Similarity	NPD3620	Phase 2
0.7075	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3022	Approved
0.7068	Intermediate Similarity	NPD3021	Approved
0.7063	Intermediate Similarity	NPD5977	Approved
0.7063	Intermediate Similarity	NPD5978	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3887	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7051	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6896	Approved
0.7047	Intermediate Similarity	NPD6895	Approved
0.7042	Intermediate Similarity	NPD2983	Phase 2
0.7042	Intermediate Similarity	NPD5327	Phase 3
0.7042	Intermediate Similarity	NPD2982	Phase 2
0.7039	Intermediate Similarity	NPD6674	Discontinued
0.7037	Intermediate Similarity	NPD7843	Approved
0.7037	Intermediate Similarity	NPD919	Approved
0.7032	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6875	Approved
0.7025	Intermediate Similarity	NPD6876	Approved
0.7021	Intermediate Similarity	NPD1611	Approved
0.702	Intermediate Similarity	NPD1375	Discontinued
0.702	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD6004	Phase 3
0.702	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6232	Discontinued
0.7011	Intermediate Similarity	NPD7296	Approved
0.7007	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4210	Discontinued
0.7	Intermediate Similarity	NPD7680	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.6994	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6331	Phase 2
0.6988	Remote Similarity	NPD7473	Discontinued
0.6987	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7110	Phase 1
0.697	Remote Similarity	NPD3926	Phase 2
0.6966	Remote Similarity	NPD5736	Approved
0.6966	Remote Similarity	NPD3018	Phase 2
0.6964	Remote Similarity	NPD7074	Phase 3
0.6957	Remote Similarity	NPD5353	Approved
0.6954	Remote Similarity	NPD2161	Phase 2
0.695	Remote Similarity	NPD3496	Discontinued
0.6948	Remote Similarity	NPD6190	Approved
0.6944	Remote Similarity	NPD5005	Approved
0.6944	Remote Similarity	NPD5006	Approved
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2067	Discontinued
0.694	Remote Similarity	NPD5451	Approved
0.6937	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1934	Approved
0.6929	Remote Similarity	NPD3025	Approved
0.6929	Remote Similarity	NPD3024	Approved
0.6928	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7315	Approved
0.6909	Remote Similarity	NPD7229	Phase 3
0.6908	Remote Similarity	NPD2346	Discontinued
0.6908	Remote Similarity	NPD2353	Approved
0.6908	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7054	Approved
0.6905	Remote Similarity	NPD5844	Phase 1
0.6899	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2801	Approved
0.6894	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3748	Approved
0.6887	Remote Similarity	NPD7033	Discontinued
0.6884	Remote Similarity	NPD6387	Discontinued
0.6883	Remote Similarity	NPD7003	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