NPASS Compound

Structure

CID254163 OpenBabel06191716052D 31 35 0 0 1 0 0 0 0 0999 V2000 -2.2634 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6701 -3.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6701 -3.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 -2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 -2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4890 -1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4890 -1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0224 -0.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0224 -0.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2688 -4.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 -2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0714 -2.0343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 -2.0343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4836 -1.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0878 -2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 -2.3479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8621 -4.9840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6810 -3.2614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 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 5.0224 -1.7253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0224 -1.7253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0714 -0.4162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 -0.4162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 -3.2614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 29 1 0 0 0 0 10 28 1 0 0 0 0 10 30 1 0 0 0 0 11 23 2 0 0 0 0 11 31 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 6 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 21 31 1 6 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.1
Volume:	401.67
LogP:	2.275
LogD:	2.466
LogS:	-4.249
# Rotatable Bonds:	6
TPSA:	116.82
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	3.685
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.393
MDCK Permeability:	1.720749969535973e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.078
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.212

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.77649688720703%
Volume Distribution (VD):	0.543
Pgp-substrate:	1.1114205121994019%

ADMET: Metabolism

CYP1A2-inhibitor:	0.337
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.24
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.762

ADMET: Excretion

Clearance (CL):	8.592
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.296
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.093
Carcinogencity:	0.77
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC254163

Natural Product ID:	NPC254163
*Common Name:**	Sanguinolignan D
IUPAC Name:	[(S)-[(3S,4R)-4-(1,3-benzodioxole-5-carbonyl)-2-oxooxolan-3-yl]-(1,3-benzodioxol-5-yl)methyl] acetate
Synonyms:	Sanguinolignan D
Standard InCHIKey:	UABDDHIGAKYFRK-ONTRVFCTSA-N
Standard InCHI:	InChI=1S/C22H18O9/c1-11(23)31-21(13-3-5-16-18(7-13)30-10-28-16)19-14(8-26-22(19)25)20(24)12-2-4-15-17(6-12)29-9-27-15/h2-7,14,19,21H,8-10H2,1H3/t14-,19-,21+/m0/s1
SMILES:	CC(=O)O[C@H](c1ccc2c(c1)OCO2)[C@@H]1[C@H](COC1=O)C(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641902
PubChem CID:	50908726
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
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	Species	Piperaceae	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	3

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	82100.0	nM	PMID[543924]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17100.0	nM	PMID[543924]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	69700.0	nM	PMID[543924]

☑ 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 NPC254163 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	398
0.1-0.2	1456
0.2-0.3	3250
0.3-0.4	7611
0.4-0.5	10510
0.5-0.6	4972
0.6-0.7	6987
0.7-0.8	7081
0.8-0.85	358
0.85-0.9	61
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC308555
0.9477	High Similarity	NPC218471
0.9477	High Similarity	NPC239818
0.9456	High Similarity	NPC153620
0.9456	High Similarity	NPC24257
0.9045	High Similarity	NPC239890
0.9045	High Similarity	NPC209411
0.8993	High Similarity	NPC15743
0.8987	High Similarity	NPC61141
0.8874	High Similarity	NPC193779
0.8874	High Similarity	NPC213482
0.8874	High Similarity	NPC30890
0.8868	High Similarity	NPC76687
0.8844	High Similarity	NPC14022
0.8808	High Similarity	NPC474158
0.8808	High Similarity	NPC327052
0.8797	High Similarity	NPC76211
0.8797	High Similarity	NPC325122
0.8792	High Similarity	NPC51681
0.879	High Similarity	NPC261484
0.8776	High Similarity	NPC102260
0.8776	High Similarity	NPC230968
0.875	High Similarity	NPC3982
0.8742	High Similarity	NPC177644
0.8742	High Similarity	NPC92693
0.8742	High Similarity	NPC191158
0.8742	High Similarity	NPC218841
0.8742	High Similarity	NPC475000
0.8726	High Similarity	NPC186316
0.871	High Similarity	NPC164082
0.871	High Similarity	NPC62354
0.8675	High Similarity	NPC474288
0.8671	High Similarity	NPC301897
0.8654	High Similarity	NPC56184
0.8654	High Similarity	NPC104353
0.8639	High Similarity	NPC19890
0.8639	High Similarity	NPC110958
0.8636	High Similarity	NPC473428
0.8625	High Similarity	NPC139876
0.8616	High Similarity	NPC76458
0.8616	High Similarity	NPC82733
0.8609	High Similarity	NPC151423
0.8609	High Similarity	NPC176586
0.8609	High Similarity	NPC210354
0.8609	High Similarity	NPC40237
0.8606	High Similarity	NPC178737
0.8599	High Similarity	NPC137813
0.8591	High Similarity	NPC166184
0.8581	High Similarity	NPC477698
0.8571	High Similarity	NPC15212
0.8571	High Similarity	NPC258322
0.8571	High Similarity	NPC205915
0.8571	High Similarity	NPC191352
0.8562	High Similarity	NPC68619
0.8562	High Similarity	NPC15764
0.8554	High Similarity	NPC474568
0.8553	High Similarity	NPC477380
0.8544	High Similarity	NPC478213
0.8544	High Similarity	NPC178195
0.8544	High Similarity	NPC57211
0.8544	High Similarity	NPC348849
0.8535	High Similarity	NPC267091
0.8535	High Similarity	NPC151425
0.8528	High Similarity	NPC180586
0.8528	High Similarity	NPC477884
0.8528	High Similarity	NPC474301
0.8528	High Similarity	NPC475738
0.8519	High Similarity	NPC478199
0.8509	High Similarity	NPC474770
0.8509	High Similarity	NPC78944
0.8506	High Similarity	NPC296575
0.8506	High Similarity	NPC224687
0.85	High Similarity	NPC474990
0.85	High Similarity	NPC226759
0.85	High Similarity	NPC19600
0.85	High Similarity	NPC477885
0.85	High Similarity	NPC258644
0.8494	Intermediate Similarity	NPC475964
0.8491	Intermediate Similarity	NPC10205
0.8481	Intermediate Similarity	NPC52623
0.8481	Intermediate Similarity	NPC68882
0.8481	Intermediate Similarity	NPC153008
0.8481	Intermediate Similarity	NPC148497
0.8471	Intermediate Similarity	NPC243891
0.8466	Intermediate Similarity	NPC475865
0.8466	Intermediate Similarity	NPC100425
0.8457	Intermediate Similarity	NPC309335
0.8457	Intermediate Similarity	NPC296540
0.8452	Intermediate Similarity	NPC25496
0.8443	Intermediate Similarity	NPC477881
0.8442	Intermediate Similarity	NPC223185
0.8438	Intermediate Similarity	NPC471405
0.8438	Intermediate Similarity	NPC115123
0.8438	Intermediate Similarity	NPC239113
0.8438	Intermediate Similarity	NPC478055
0.8438	Intermediate Similarity	NPC155063
0.8435	Intermediate Similarity	NPC227160
0.8435	Intermediate Similarity	NPC82111
0.8431	Intermediate Similarity	NPC137920
0.8431	Intermediate Similarity	NPC125134
0.8431	Intermediate Similarity	NPC86455
0.8428	Intermediate Similarity	NPC287504
0.8428	Intermediate Similarity	NPC273578
0.8428	Intermediate Similarity	NPC136757
0.8428	Intermediate Similarity	NPC25127
0.8428	Intermediate Similarity	NPC54179
0.8424	Intermediate Similarity	NPC42230
0.8424	Intermediate Similarity	NPC474948
0.8421	Intermediate Similarity	NPC28398
0.8418	Intermediate Similarity	NPC36130
0.8418	Intermediate Similarity	NPC279061
0.8418	Intermediate Similarity	NPC477699
0.8418	Intermediate Similarity	NPC220577
0.8418	Intermediate Similarity	NPC134905
0.8415	Intermediate Similarity	NPC475953
0.8405	Intermediate Similarity	NPC19948
0.8395	Intermediate Similarity	NPC43971
0.8395	Intermediate Similarity	NPC74749
0.8395	Intermediate Similarity	NPC19554
0.8377	Intermediate Similarity	NPC474036
0.8377	Intermediate Similarity	NPC46880
0.8375	Intermediate Similarity	NPC3273
0.8375	Intermediate Similarity	NPC478238
0.8367	Intermediate Similarity	NPC271208
0.8367	Intermediate Similarity	NPC233224
0.8354	Intermediate Similarity	NPC210642
0.8354	Intermediate Similarity	NPC474975
0.8354	Intermediate Similarity	NPC303519
0.8354	Intermediate Similarity	NPC32079
0.8354	Intermediate Similarity	NPC100420
0.8354	Intermediate Similarity	NPC477700
0.8354	Intermediate Similarity	NPC13985
0.8344	Intermediate Similarity	NPC34376
0.8344	Intermediate Similarity	NPC127827
0.8344	Intermediate Similarity	NPC262455
0.8344	Intermediate Similarity	NPC177476
0.8344	Intermediate Similarity	NPC24193
0.8344	Intermediate Similarity	NPC319749
0.8333	Intermediate Similarity	NPC50430
0.8323	Intermediate Similarity	NPC261090
0.8323	Intermediate Similarity	NPC473900
0.8323	Intermediate Similarity	NPC477883
0.8313	Intermediate Similarity	NPC471180
0.8313	Intermediate Similarity	NPC194095
0.8313	Intermediate Similarity	NPC327032
0.8313	Intermediate Similarity	NPC244371
0.8313	Intermediate Similarity	NPC191046
0.8313	Intermediate Similarity	NPC79322
0.8303	Intermediate Similarity	NPC474647
0.8303	Intermediate Similarity	NPC187923
0.8302	Intermediate Similarity	NPC118332
0.8301	Intermediate Similarity	NPC218092
0.8301	Intermediate Similarity	NPC246474
0.8301	Intermediate Similarity	NPC162851
0.8299	Intermediate Similarity	NPC476748
0.8294	Intermediate Similarity	NPC477882
0.8294	Intermediate Similarity	NPC477880
0.8293	Intermediate Similarity	NPC280778
0.8291	Intermediate Similarity	NPC158635
0.8291	Intermediate Similarity	NPC475722
0.8291	Intermediate Similarity	NPC229882
0.8291	Intermediate Similarity	NPC475170
0.8284	Intermediate Similarity	NPC469438
0.8282	Intermediate Similarity	NPC96593
0.8282	Intermediate Similarity	NPC472961
0.8282	Intermediate Similarity	NPC131557
0.8282	Intermediate Similarity	NPC472962
0.828	Intermediate Similarity	NPC181464
0.828	Intermediate Similarity	NPC472969
0.8278	Intermediate Similarity	NPC209229
0.8278	Intermediate Similarity	NPC11453
0.8272	Intermediate Similarity	NPC475663
0.8272	Intermediate Similarity	NPC286919
0.8272	Intermediate Similarity	NPC310206
0.8272	Intermediate Similarity	NPC472860
0.8269	Intermediate Similarity	NPC87295
0.8267	Intermediate Similarity	NPC311339
0.8267	Intermediate Similarity	NPC37065
0.8261	Intermediate Similarity	NPC234730
0.8261	Intermediate Similarity	NPC284353
0.8258	Intermediate Similarity	NPC239608
0.8258	Intermediate Similarity	NPC141569
0.8258	Intermediate Similarity	NPC166884
0.8258	Intermediate Similarity	NPC477701
0.8258	Intermediate Similarity	NPC473090
0.8258	Intermediate Similarity	NPC46161
0.8255	Intermediate Similarity	NPC158526
0.8255	Intermediate Similarity	NPC33611
0.8255	Intermediate Similarity	NPC16830
0.8255	Intermediate Similarity	NPC100223
0.8255	Intermediate Similarity	NPC129687
0.8255	Intermediate Similarity	NPC171928
0.8253	Intermediate Similarity	NPC471923
0.825	Intermediate Similarity	NPC44730
0.825	Intermediate Similarity	NPC157898
0.825	Intermediate Similarity	NPC474514
0.825	Intermediate Similarity	NPC475116
0.825	Intermediate Similarity	NPC292460
0.8242	Intermediate Similarity	NPC91288
0.8242	Intermediate Similarity	NPC89131

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 NPC254163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	858
0.2-0.3	1699
0.3-0.4	2619
0.4-0.5	2024
0.5-0.6	1083
0.6-0.7	416
0.7-0.8	120
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD6980	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3818	Discontinued
0.8171	Intermediate Similarity	NPD5494	Approved
0.8098	Intermediate Similarity	NPD4966	Approved
0.8098	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7931	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD37	Approved
0.7907	Intermediate Similarity	NPD7685	Pre-registration
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD6385	Approved
0.7744	Intermediate Similarity	NPD6386	Approved
0.7733	Intermediate Similarity	NPD7054	Approved
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1934	Approved
0.7688	Intermediate Similarity	NPD7472	Approved
0.7679	Intermediate Similarity	NPD919	Approved
0.7674	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1933	Approved
0.7602	Intermediate Similarity	NPD5242	Approved
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD2801	Approved
0.7545	Intermediate Similarity	NPD7819	Suspended
0.7545	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6797	Phase 2
0.7532	Intermediate Similarity	NPD2796	Approved
0.7531	Intermediate Similarity	NPD6799	Approved
0.7517	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD4420	Approved
0.7485	Intermediate Similarity	NPD1247	Approved
0.747	Intermediate Similarity	NPD6599	Discontinued
0.7457	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6166	Phase 2
0.7457	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5844	Phase 1
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7075	Discontinued
0.741	Intermediate Similarity	NPD7458	Discontinued
0.7394	Intermediate Similarity	NPD920	Approved
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7383	Intermediate Similarity	NPD17	Approved
0.7381	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD4380	Phase 2
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.734	Intermediate Similarity	NPD5005	Approved
0.734	Intermediate Similarity	NPD5006	Approved
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD2438	Suspended
0.7312	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD3226	Approved
0.7301	Intermediate Similarity	NPD6190	Approved
0.7297	Intermediate Similarity	NPD5536	Phase 2
0.7294	Intermediate Similarity	NPD5402	Approved
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7262	Intermediate Similarity	NPD7028	Phase 2
0.7255	Intermediate Similarity	NPD1876	Approved
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4110	Phase 3
0.7239	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3972	Approved
0.7237	Intermediate Similarity	NPD1608	Approved
0.7235	Intermediate Similarity	NPD1465	Phase 2
0.7232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7296	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7411	Suspended
0.7212	Intermediate Similarity	NPD1511	Approved
0.7195	Intermediate Similarity	NPD3887	Approved
0.7184	Intermediate Similarity	NPD8127	Discontinued
0.7178	Intermediate Similarity	NPD1243	Approved
0.7175	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD6808	Phase 2
0.7143	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD1512	Approved
0.7118	Intermediate Similarity	NPD6873	Phase 2
0.7117	Intermediate Similarity	NPD1549	Phase 2
0.7115	Intermediate Similarity	NPD9494	Approved
0.7107	Intermediate Similarity	NPD2979	Phase 3
0.7107	Intermediate Similarity	NPD1240	Approved
0.7093	Intermediate Similarity	NPD5978	Approved
0.7093	Intermediate Similarity	NPD5977	Approved
0.7093	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3764	Approved
0.7088	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7066	Intermediate Similarity	NPD5401	Approved
0.7066	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7055	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7031	Intermediate Similarity	NPD7680	Approved
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.7024	Intermediate Similarity	NPD6273	Approved
0.7019	Intermediate Similarity	NPD1607	Approved
0.7011	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2309	Approved
0.6981	Remote Similarity	NPD2313	Discontinued
0.6981	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3146	Approved
0.6963	Remote Similarity	NPD6777	Approved
0.6963	Remote Similarity	NPD6776	Approved
0.6963	Remote Similarity	NPD6779	Approved
0.6963	Remote Similarity	NPD6781	Approved
0.6963	Remote Similarity	NPD6778	Approved
0.6963	Remote Similarity	NPD6782	Approved
0.6963	Remote Similarity	NPD6780	Approved
0.6951	Remote Similarity	NPD2353	Approved
0.6951	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3787	Discontinued
0.6948	Remote Similarity	NPD1281	Approved
0.6948	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1653	Approved
0.6939	Remote Similarity	NPD8151	Discontinued
0.6935	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7033	Discontinued
0.6928	Remote Similarity	NPD3750	Approved
0.6918	Remote Similarity	NPD3027	Phase 3
0.6911	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9545	Approved
0.6894	Remote Similarity	NPD943	Approved
0.6893	Remote Similarity	NPD6959	Discontinued
0.6889	Remote Similarity	NPD7799	Discontinued
0.6879	Remote Similarity	NPD6280	Approved
0.6879	Remote Similarity	NPD3266	Approved
0.6879	Remote Similarity	NPD6279	Approved
0.6879	Remote Similarity	NPD3267	Approved
0.6871	Remote Similarity	NPD7097	Phase 1
0.6868	Remote Similarity	NPD5953	Discontinued
0.6864	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5585	Approved
0.6857	Remote Similarity	NPD7768	Phase 2
0.6856	Remote Similarity	NPD7696	Phase 3
0.6856	Remote Similarity	NPD7697	Approved
0.6856	Remote Similarity	NPD7698	Approved
0.6832	Remote Similarity	NPD6233	Phase 2
0.6831	Remote Similarity	NPD7038	Approved
0.6831	Remote Similarity	NPD7039	Approved
0.6828	Remote Similarity	NPD8150	Discontinued
0.6824	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7871	Phase 2
0.6821	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7874	Approved
0.6815	Remote Similarity	NPD1283	Approved
0.68	Remote Similarity	NPD1241	Discontinued
0.6788	Remote Similarity	NPD1551	Phase 2
0.6788	Remote Similarity	NPD2531	Phase 2
0.6786	Remote Similarity	NPD2354	Approved
0.6786	Remote Similarity	NPD7999	Approved
0.6778	Remote Similarity	NPD2403	Approved
0.677	Remote Similarity	NPD3268	Approved
0.677	Remote Similarity	NPD6798	Discontinued
0.6766	Remote Similarity	NPD7930	Approved
0.6766	Remote Similarity	NPD2800	Approved
0.6761	Remote Similarity	NPD5019	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