NPASS Compound

Structure

NPC125134 OpenBabel07101718312D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.2072 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 3.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4752 3.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6092 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 3.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 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 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 25 1 0 0 0 0 10 26 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 2 1 6 0 0 0 12 21 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 13 1 1 0 0 0 21 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	363.042
LogP:	3.775
LogD:	3.565
LogS:	-6.01
# Rotatable Bonds:	3
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.833
Synthetic Accessibility Score:	3.421
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:	-4.876
MDCK Permeability:	5.153654274181463e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.193

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	98.28966522216797%
Volume Distribution (VD):	1.001
Pgp-substrate:	2.0909435749053955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.808
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.877

ADMET: Excretion

Clearance (CL):	12.205
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.385
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.542
Skin Sensitization:	0.037
Carcinogencity:	0.765
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC125134

Natural Product ID:	NPC125134
*Common Name:**	(7'r,8S,8's)-3',4'-Dimethoxy-4,5-Methylenodioxy-2,7'-Cyclolignan-7-One
IUPAC Name:	(6S,7S,8R)-8-(3,4-dimethoxyphenyl)-6,7-dimethyl-7,8-dihydro-6H-benzo[f][1,3]benzodioxol-5-one
Synonyms:
Standard InCHIKey:	QJKIOLPHXOZLDC-XAAFQQQXSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-11-12(2)21(22)15-9-19-18(25-10-26-19)8-14(15)20(11)13-5-6-16(23-3)17(7-13)24-4/h5-9,11-12,20H,10H2,1-4H3/t11-,12+,20-/m1/s1
SMILES:	COc1cc(ccc1OC)[C@H]1[C@H](C)[C@H](C)C(=O)c2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521156
PubChem CID:	14034478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin 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
NPO12054	Holostylis reniformis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17438049]
NPO12054	Holostylis reniformis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20961092]
NPO12054	Holostylis reniformis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12054	Holostylis reniformis	Species	Aristolochiaceae	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	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8000.0	nM	PMID[470713]
NPT27	Others	Unspecified		Activity	=	30.0	%	PMID[470713]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	19700.0	nM	PMID[470713]

☑ 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 NPC125134 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	422
0.1-0.2	1594
0.2-0.3	3592
0.3-0.4	9213
0.4-0.5	9449
0.5-0.6	3407
0.6-0.7	9974
0.7-0.8	4797
0.8-0.85	197
0.85-0.9	37
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86455
1.0	High Similarity	NPC137920
0.9481	High Similarity	NPC95485
0.9481	High Similarity	NPC88065
0.9481	High Similarity	NPC89504
0.9291	High Similarity	NPC229787
0.9143	High Similarity	NPC28398
0.9085	High Similarity	NPC46880
0.9034	High Similarity	NPC127827
0.9014	High Similarity	NPC192597
0.9014	High Similarity	NPC229218
0.9014	High Similarity	NPC141817
0.9014	High Similarity	NPC169214
0.9014	High Similarity	NPC176030
0.898	High Similarity	NPC118332
0.8973	High Similarity	NPC37220
0.8936	High Similarity	NPC223336
0.8889	High Similarity	NPC286683
0.8844	High Similarity	NPC475722
0.8776	High Similarity	NPC24193
0.8767	High Similarity	NPC153620
0.8767	High Similarity	NPC24257
0.8759	High Similarity	NPC327052
0.8758	High Similarity	NPC209411
0.8758	High Similarity	NPC239890
0.875	High Similarity	NPC68619
0.875	High Similarity	NPC125713
0.8742	High Similarity	NPC109765
0.8741	High Similarity	NPC218092
0.8741	High Similarity	NPC246474
0.8741	High Similarity	NPC17348
0.8741	High Similarity	NPC162851
0.8725	High Similarity	NPC220577
0.8707	High Similarity	NPC181464
0.8684	High Similarity	NPC202495
0.8676	High Similarity	NPC177925
0.8667	High Similarity	NPC30216
0.863	High Similarity	NPC472836
0.8613	High Similarity	NPC177167
0.8613	High Similarity	NPC64948
0.8601	High Similarity	NPC470962
0.8593	High Similarity	NPC474691
0.8543	High Similarity	NPC308555
0.8511	High Similarity	NPC205915
0.8497	Intermediate Similarity	NPC115123
0.8497	Intermediate Similarity	NPC239113
0.8487	Intermediate Similarity	NPC54179
0.8467	Intermediate Similarity	NPC261322
0.8462	Intermediate Similarity	NPC230968
0.8462	Intermediate Similarity	NPC102260
0.8446	Intermediate Similarity	NPC73416
0.8446	Intermediate Similarity	NPC160777
0.8446	Intermediate Similarity	NPC224687
0.8446	Intermediate Similarity	NPC296575
0.844	Intermediate Similarity	NPC183103
0.8431	Intermediate Similarity	NPC254163
0.8431	Intermediate Similarity	NPC234730
0.8429	Intermediate Similarity	NPC477694
0.8429	Intermediate Similarity	NPC477705
0.8389	Intermediate Similarity	NPC101755
0.8389	Intermediate Similarity	NPC304687
0.8389	Intermediate Similarity	NPC104024
0.8389	Intermediate Similarity	NPC80230
0.8389	Intermediate Similarity	NPC65574
0.8387	Intermediate Similarity	NPC325122
0.8378	Intermediate Similarity	NPC309169
0.8378	Intermediate Similarity	NPC196941
0.8378	Intermediate Similarity	NPC308006
0.8377	Intermediate Similarity	NPC261484
0.837	Intermediate Similarity	NPC225245
0.8369	Intermediate Similarity	NPC164295
0.8369	Intermediate Similarity	NPC477706
0.8367	Intermediate Similarity	NPC472564
0.8366	Intermediate Similarity	NPC478213
0.8356	Intermediate Similarity	NPC29599
0.8355	Intermediate Similarity	NPC104353
0.8354	Intermediate Similarity	NPC477884
0.8345	Intermediate Similarity	NPC223807
0.8345	Intermediate Similarity	NPC100129
0.8344	Intermediate Similarity	NPC300983
0.8333	Intermediate Similarity	NPC78944
0.8333	Intermediate Similarity	NPC262804
0.8333	Intermediate Similarity	NPC52692
0.8333	Intermediate Similarity	NPC120066
0.8333	Intermediate Similarity	NPC65784
0.8333	Intermediate Similarity	NPC40654
0.8323	Intermediate Similarity	NPC310206
0.8323	Intermediate Similarity	NPC19600
0.8323	Intermediate Similarity	NPC474990
0.8322	Intermediate Similarity	NPC189054
0.8322	Intermediate Similarity	NPC30890
0.8322	Intermediate Similarity	NPC110958
0.8322	Intermediate Similarity	NPC19890
0.8312	Intermediate Similarity	NPC3273
0.8312	Intermediate Similarity	NPC478238
0.831	Intermediate Similarity	NPC153453
0.831	Intermediate Similarity	NPC227002
0.8301	Intermediate Similarity	NPC68882
0.8301	Intermediate Similarity	NPC164912
0.8301	Intermediate Similarity	NPC153008
0.8301	Intermediate Similarity	NPC148497
0.8296	Intermediate Similarity	NPC344161
0.8291	Intermediate Similarity	NPC100425
0.8291	Intermediate Similarity	NPC100420
0.8289	Intermediate Similarity	NPC295977
0.8289	Intermediate Similarity	NPC58310
0.8278	Intermediate Similarity	NPC474306
0.8278	Intermediate Similarity	NPC177476
0.8278	Intermediate Similarity	NPC472839
0.8278	Intermediate Similarity	NPC262455
0.8278	Intermediate Similarity	NPC476058
0.8278	Intermediate Similarity	NPC475848
0.8273	Intermediate Similarity	NPC474737
0.8269	Intermediate Similarity	NPC474043
0.8258	Intermediate Similarity	NPC473900
0.8258	Intermediate Similarity	NPC213401
0.8258	Intermediate Similarity	NPC301897
0.8255	Intermediate Similarity	NPC91694
0.8255	Intermediate Similarity	NPC300603
0.8248	Intermediate Similarity	NPC256167
0.8247	Intermediate Similarity	NPC57211
0.8247	Intermediate Similarity	NPC273578
0.8239	Intermediate Similarity	NPC239134
0.8239	Intermediate Similarity	NPC474301
0.8235	Intermediate Similarity	NPC302783
0.8235	Intermediate Similarity	NPC472838
0.8235	Intermediate Similarity	NPC306011
0.8235	Intermediate Similarity	NPC78505
0.8235	Intermediate Similarity	NPC144283
0.8235	Intermediate Similarity	NPC279061
0.8235	Intermediate Similarity	NPC473201
0.8235	Intermediate Similarity	NPC118427
0.8235	Intermediate Similarity	NPC474414
0.8231	Intermediate Similarity	NPC78987
0.8231	Intermediate Similarity	NPC51681
0.8231	Intermediate Similarity	NPC82336
0.8228	Intermediate Similarity	NPC19948
0.8228	Intermediate Similarity	NPC116838
0.8228	Intermediate Similarity	NPC61141
0.8228	Intermediate Similarity	NPC22130
0.8224	Intermediate Similarity	NPC237441
0.8224	Intermediate Similarity	NPC149505
0.8224	Intermediate Similarity	NPC474305
0.8219	Intermediate Similarity	NPC178290
0.8217	Intermediate Similarity	NPC139876
0.8205	Intermediate Similarity	NPC82733
0.8205	Intermediate Similarity	NPC258644
0.8205	Intermediate Similarity	NPC76458
0.82	Intermediate Similarity	NPC87295
0.8188	Intermediate Similarity	NPC239608
0.8188	Intermediate Similarity	NPC15743
0.8188	Intermediate Similarity	NPC46161
0.8182	Intermediate Similarity	NPC52623
0.8176	Intermediate Similarity	NPC475865
0.8175	Intermediate Similarity	NPC80241
0.8175	Intermediate Similarity	NPC301641
0.817	Intermediate Similarity	NPC13985
0.817	Intermediate Similarity	NPC234152
0.817	Intermediate Similarity	NPC210642
0.8169	Intermediate Similarity	NPC66905
0.8165	Intermediate Similarity	NPC258322
0.8165	Intermediate Similarity	NPC15212
0.8165	Intermediate Similarity	NPC191352
0.8165	Intermediate Similarity	NPC319749
0.8153	Intermediate Similarity	NPC15764
0.8153	Intermediate Similarity	NPC113055
0.8151	Intermediate Similarity	NPC186647
0.8146	Intermediate Similarity	NPC39361
0.8141	Intermediate Similarity	NPC261090
0.8141	Intermediate Similarity	NPC155063
0.8141	Intermediate Similarity	NPC477380
0.8133	Intermediate Similarity	NPC474158
0.8129	Intermediate Similarity	NPC244371
0.8125	Intermediate Similarity	NPC470406
0.8117	Intermediate Similarity	NPC267091
0.8117	Intermediate Similarity	NPC124842
0.8113	Intermediate Similarity	NPC280778
0.8113	Intermediate Similarity	NPC478199
0.8108	Intermediate Similarity	NPC282291
0.8108	Intermediate Similarity	NPC166137
0.8108	Intermediate Similarity	NPC323601
0.8105	Intermediate Similarity	NPC12854
0.8101	Intermediate Similarity	NPC474770
0.8101	Intermediate Similarity	NPC218471
0.8101	Intermediate Similarity	NPC239818
0.8098	Intermediate Similarity	NPC469506
0.8092	Intermediate Similarity	NPC474999
0.8092	Intermediate Similarity	NPC58373
0.8089	Intermediate Similarity	NPC477885
0.8085	Intermediate Similarity	NPC428300
0.8082	Intermediate Similarity	NPC90431
0.8079	Intermediate Similarity	NPC225351
0.8077	Intermediate Similarity	NPC202249
0.8077	Intermediate Similarity	NPC284353
0.8077	Intermediate Similarity	NPC188962
0.8077	Intermediate Similarity	NPC42871
0.8075	Intermediate Similarity	NPC471923
0.8074	Intermediate Similarity	NPC469954
0.8069	Intermediate Similarity	NPC311339
0.8069	Intermediate Similarity	NPC45404

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 NPC125134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	968
0.2-0.3	1347
0.3-0.4	2583
0.4-0.5	2113
0.5-0.6	1114
0.6-0.7	545
0.7-0.8	109
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
0.8707	High Similarity	NPD6980	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD7028	Phase 2
0.8105	Intermediate Similarity	NPD7458	Discontinued
0.8065	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD1876	Approved
0.7986	Intermediate Similarity	NPD3972	Approved
0.7962	Intermediate Similarity	NPD5977	Approved
0.7962	Intermediate Similarity	NPD5978	Approved
0.7941	Intermediate Similarity	NPD5536	Phase 2
0.7911	Intermediate Similarity	NPD4966	Approved
0.7911	Intermediate Similarity	NPD4965	Approved
0.7911	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD1651	Approved
0.7812	Intermediate Similarity	NPD6234	Discontinued
0.7786	Intermediate Similarity	NPD1281	Approved
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7762	Intermediate Similarity	NPD2798	Approved
0.7751	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7677	Intermediate Similarity	NPD6273	Approved
0.766	Intermediate Similarity	NPD3705	Approved
0.7635	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD1283	Approved
0.7622	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8032	Phase 2
0.7616	Intermediate Similarity	NPD1471	Phase 3
0.7586	Intermediate Similarity	NPD9494	Approved
0.7582	Intermediate Similarity	NPD7003	Approved
0.7568	Intermediate Similarity	NPD2979	Phase 3
0.7552	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2438	Suspended
0.7547	Intermediate Similarity	NPD6873	Phase 2
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7438	Intermediate Similarity	NPD6385	Approved
0.7438	Intermediate Similarity	NPD6386	Approved
0.7432	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7685	Pre-registration
0.741	Intermediate Similarity	NPD3926	Phase 2
0.7403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4110	Phase 3
0.7355	Intermediate Similarity	NPD8166	Discontinued
0.7346	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD2801	Approved
0.7324	Intermediate Similarity	NPD3024	Approved
0.7324	Intermediate Similarity	NPD3025	Approved
0.732	Intermediate Similarity	NPD2935	Discontinued
0.732	Intermediate Similarity	NPD2531	Phase 2
0.7312	Intermediate Similarity	NPD3226	Approved
0.731	Intermediate Similarity	NPD7240	Approved
0.7301	Intermediate Similarity	NPD3817	Phase 2
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.7289	Intermediate Similarity	NPD8127	Discontinued
0.7285	Intermediate Similarity	NPD3657	Discovery
0.7284	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD919	Approved
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD3023	Approved
0.7222	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3026	Approved
0.7222	Intermediate Similarity	NPD7110	Phase 1
0.7219	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3620	Phase 2
0.7208	Intermediate Similarity	NPD2796	Approved
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5691	Approved
0.7202	Intermediate Similarity	NPD5242	Approved
0.7197	Intermediate Similarity	NPD3887	Approved
0.7195	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7472	Approved
0.7188	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7184	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2353	Approved
0.716	Intermediate Similarity	NPD6875	Approved
0.716	Intermediate Similarity	NPD6876	Approved
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7126	Intermediate Similarity	NPD8313	Approved
0.7126	Intermediate Similarity	NPD8312	Approved
0.7123	Intermediate Similarity	NPD1608	Approved
0.7122	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6559	Discontinued
0.7108	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3266	Approved
0.7095	Intermediate Similarity	NPD3267	Approved
0.7095	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD2309	Approved
0.7086	Intermediate Similarity	NPD5109	Approved
0.7086	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD5110	Phase 2
0.7086	Intermediate Similarity	NPD5111	Phase 2
0.7083	Intermediate Similarity	NPD1357	Approved
0.7075	Intermediate Similarity	NPD5327	Phase 3
0.707	Intermediate Similarity	NPD6674	Discontinued
0.7069	Intermediate Similarity	NPD7808	Phase 3
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD6166	Phase 2
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD447	Suspended
0.7059	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6797	Phase 2
0.7034	Intermediate Similarity	NPD2932	Approved
0.7032	Intermediate Similarity	NPD1510	Phase 2
0.7032	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3750	Approved
0.702	Intermediate Similarity	NPD7095	Approved
0.7013	Intermediate Similarity	NPD1607	Approved
0.7013	Intermediate Similarity	NPD2492	Phase 1
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD4060	Phase 1
0.6993	Remote Similarity	NPD1240	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD4140	Approved
0.6988	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD2354	Approved
0.6974	Remote Similarity	NPD6798	Discontinued
0.6974	Remote Similarity	NPD3268	Approved
0.6957	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6832	Phase 2
0.6951	Remote Similarity	NPD4380	Phase 2
0.695	Remote Similarity	NPD5535	Approved
0.694	Remote Similarity	NPD4420	Approved
0.6939	Remote Similarity	NPD1201	Approved
0.6933	Remote Similarity	NPD4624	Approved
0.6932	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4108	Discontinued
0.6914	Remote Similarity	NPD1512	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6909	Remote Similarity	NPD7411	Suspended
0.6905	Remote Similarity	NPD7075	Discontinued
0.6903	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD943	Approved
0.6883	Remote Similarity	NPD3142	Approved
0.6883	Remote Similarity	NPD3140	Approved
0.6882	Remote Similarity	NPD6959	Discontinued
0.6879	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD6190	Approved
0.6871	Remote Similarity	NPD3640	Phase 3
0.6871	Remote Similarity	NPD3639	Approved
0.6871	Remote Similarity	NPD3641	Approved
0.6871	Remote Similarity	NPD920	Approved
0.6868	Remote Similarity	NPD2746	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2745	Approved
0.6867	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD6280	Approved
0.6867	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD6279	Approved
0.6865	Remote Similarity	NPD6777	Approved
0.6865	Remote Similarity	NPD6779	Approved
0.6865	Remote Similarity	NPD6782	Approved
0.6865	Remote Similarity	NPD6780	Approved
0.6865	Remote Similarity	NPD6778	Approved
0.6865	Remote Similarity	NPD6781	Approved
0.6865	Remote Similarity	NPD6776	Approved
0.6859	Remote Similarity	NPD7097	Phase 1
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1243	Approved
0.6852	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5585	Approved
0.6846	Remote Similarity	NPD3600	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