NPASS Compound

Structure

CID37183 OpenBabel06191715362D 30 33 0 0 0 0 0 0 0 0999 V2000 2.5165 4.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7578 4.4976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6799 3.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2742 2.8091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 2.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0288 1.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5159 2.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6765 0.9681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6774 0.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -1.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -1.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6370 3.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3277 2.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5157 1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3537 0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5151 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5152 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8382 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8385 -0.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 1.4745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3812 -1.9516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3808 0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5150 -1.4528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 21 2 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 29 1 0 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.18
Volume:	426.953
LogP:	6.595
LogD:	4.227
LogS:	-3.555
# Rotatable Bonds:	4
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	3.285
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006
MDCK Permeability:	1.3993657375976909e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.416
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	88.95781707763672%
Volume Distribution (VD):	1.697
Pgp-substrate:	11.911025047302246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.696
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.37
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	17.397
Half-life (T1/2):	0.41

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.329
Rat Oral Acute Toxicity:	0.766
Maximum Recommended Daily Dose:	0.281
Skin Sensitization:	0.857
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.427
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC37183

Natural Product ID:	NPC37183
*Common Name:**	Lespecyrtin F2
IUPAC Name:	2,10-bis(3-methylbut-2-enyl)-6H-[1]benzofuro[3,2-c]chromene-3,8,9-triol
Synonyms:	Lespecyrtin F2
Standard InCHIKey:	LGLLDPCJEPLYCU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-13(2)5-7-15-9-18-22(11-20(15)26)29-12-19-17-10-21(27)23(28)16(8-6-14(3)4)24(17)30-25(18)19/h5-6,9-11,26-28H,7-8,12H2,1-4H3
SMILES:	CC(=CCc1cc2-c3c(COc2cc1O)c1cc(c(c(CC=C(C)C)c1o3)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551908
PubChem CID:	25208758
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	15900.0	nM	PMID[480060]

☑ 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 NPC37183 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	419
0.1-0.2	1679
0.2-0.3	4009
0.3-0.4	10119
0.4-0.5	8270
0.5-0.6	3550
0.6-0.7	4934
0.7-0.8	5217
0.8-0.85	2478
0.85-0.9	1478
0.9-0.95	532
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC277480
0.9627	High Similarity	NPC310794
0.9623	High Similarity	NPC247973
0.9623	High Similarity	NPC50394
0.9557	High Similarity	NPC472278
0.9557	High Similarity	NPC329669
0.9557	High Similarity	NPC473313
0.9506	High Similarity	NPC261471
0.9503	High Similarity	NPC218533
0.9503	High Similarity	NPC131866
0.9503	High Similarity	NPC78830
0.9497	High Similarity	NPC291110
0.9494	High Similarity	NPC84515
0.9494	High Similarity	NPC312056
0.9484	High Similarity	NPC113906
0.9444	High Similarity	NPC28589
0.9444	High Similarity	NPC248593
0.9434	High Similarity	NPC133065
0.943	High Similarity	NPC188486
0.9427	High Similarity	NPC196879
0.9387	High Similarity	NPC37606
0.9379	High Similarity	NPC86477
0.9375	High Similarity	NPC473286
0.9375	High Similarity	NPC326520
0.9375	High Similarity	NPC39306
0.9371	High Similarity	NPC81679
0.9363	High Similarity	NPC262286
0.9363	High Similarity	NPC36852
0.9355	High Similarity	NPC5871
0.9355	High Similarity	NPC125300
0.9325	High Similarity	NPC174700
0.9317	High Similarity	NPC170245
0.9313	High Similarity	NPC18100
0.9308	High Similarity	NPC472275
0.9308	High Similarity	NPC74854
0.9308	High Similarity	NPC45124
0.9308	High Similarity	NPC30655
0.9304	High Similarity	NPC172770
0.9304	High Similarity	NPC16935
0.9304	High Similarity	NPC185258
0.9299	High Similarity	NPC45131
0.9299	High Similarity	NPC142339
0.9299	High Similarity	NPC138243
0.9295	High Similarity	NPC1477
0.9295	High Similarity	NPC213608
0.9273	High Similarity	NPC49667
0.9273	High Similarity	NPC164384
0.9273	High Similarity	NPC8127
0.9255	High Similarity	NPC36320
0.9255	High Similarity	NPC45449
0.9255	High Similarity	NPC472277
0.9255	High Similarity	NPC38914
0.9245	High Similarity	NPC14353
0.9245	High Similarity	NPC56085
0.9245	High Similarity	NPC228785
0.9241	High Similarity	NPC236796
0.9241	High Similarity	NPC79053
0.9241	High Similarity	NPC78225
0.9241	High Similarity	NPC223787
0.9241	High Similarity	NPC469584
0.9231	High Similarity	NPC106976
0.9212	High Similarity	NPC287243
0.9207	High Similarity	NPC307286
0.9198	High Similarity	NPC235610
0.9193	High Similarity	NPC1755
0.9193	High Similarity	NPC475985
0.9193	High Similarity	NPC205265
0.9193	High Similarity	NPC124038
0.9193	High Similarity	NPC7483
0.9193	High Similarity	NPC39305
0.9193	High Similarity	NPC1706
0.9193	High Similarity	NPC273959
0.9193	High Similarity	NPC263092
0.9193	High Similarity	NPC59295
0.9193	High Similarity	NPC41301
0.9193	High Similarity	NPC472281
0.9187	High Similarity	NPC40491
0.9187	High Similarity	NPC32694
0.9187	High Similarity	NPC266314
0.9187	High Similarity	NPC278052
0.9187	High Similarity	NPC61010
0.9182	High Similarity	NPC329091
0.9182	High Similarity	NPC250214
0.9182	High Similarity	NPC100123
0.9182	High Similarity	NPC95936
0.9177	High Similarity	NPC191146
0.9177	High Similarity	NPC68093
0.9177	High Similarity	NPC472916
0.9172	High Similarity	NPC304322
0.9172	High Similarity	NPC298692
0.9172	High Similarity	NPC192083
0.9172	High Similarity	NPC213896
0.9172	High Similarity	NPC183874
0.9172	High Similarity	NPC74924
0.9172	High Similarity	NPC89474
0.9167	High Similarity	NPC170169
0.9162	High Similarity	NPC183843
0.9161	High Similarity	NPC178202
0.9152	High Similarity	NPC65885
0.9152	High Similarity	NPC216842
0.9152	High Similarity	NPC476640
0.9152	High Similarity	NPC473834
0.9152	High Similarity	NPC82217
0.9146	High Similarity	NPC472276
0.9141	High Similarity	NPC241820
0.9136	High Similarity	NPC300053
0.9136	High Similarity	NPC108433
0.9136	High Similarity	NPC29411
0.913	High Similarity	NPC329760
0.913	High Similarity	NPC272722
0.913	High Similarity	NPC472448
0.913	High Similarity	NPC470694
0.913	High Similarity	NPC238995
0.913	High Similarity	NPC83922
0.913	High Similarity	NPC220912
0.9125	High Similarity	NPC304839
0.9125	High Similarity	NPC476980
0.9125	High Similarity	NPC235018
0.9125	High Similarity	NPC45146
0.9125	High Similarity	NPC472624
0.9125	High Similarity	NPC220582
0.9125	High Similarity	NPC320359
0.9125	High Similarity	NPC476283
0.9125	High Similarity	NPC475886
0.9125	High Similarity	NPC328102
0.9125	High Similarity	NPC119224
0.9125	High Similarity	NPC474287
0.9119	High Similarity	NPC474208
0.9119	High Similarity	NPC129684
0.9119	High Similarity	NPC165977
0.9119	High Similarity	NPC472914
0.9119	High Similarity	NPC99597
0.9119	High Similarity	NPC156057
0.9119	High Similarity	NPC245758
0.9119	High Similarity	NPC299520
0.9119	High Similarity	NPC48208
0.9119	High Similarity	NPC162869
0.9119	High Similarity	NPC472911
0.9119	High Similarity	NPC181960
0.9119	High Similarity	NPC475267
0.9119	High Similarity	NPC300727
0.9119	High Similarity	NPC472910
0.9119	High Similarity	NPC217677
0.9119	High Similarity	NPC210084
0.9119	High Similarity	NPC222814
0.9119	High Similarity	NPC196448
0.9119	High Similarity	NPC291508
0.9119	High Similarity	NPC474836
0.9119	High Similarity	NPC472913
0.9119	High Similarity	NPC241904
0.9119	High Similarity	NPC96167
0.9119	High Similarity	NPC65504
0.9118	High Similarity	NPC139683
0.9118	High Similarity	NPC73929
0.9118	High Similarity	NPC47905
0.9114	High Similarity	NPC152951
0.9114	High Similarity	NPC57674
0.9114	High Similarity	NPC477503
0.9114	High Similarity	NPC321779
0.9114	High Similarity	NPC198490
0.9114	High Similarity	NPC2928
0.9114	High Similarity	NPC134287
0.9114	High Similarity	NPC168247
0.9114	High Similarity	NPC117992
0.9114	High Similarity	NPC45849
0.9114	High Similarity	NPC470327
0.9114	High Similarity	NPC200761
0.9114	High Similarity	NPC130589
0.9114	High Similarity	NPC230149
0.9114	High Similarity	NPC148938
0.9108	High Similarity	NPC249570
0.9108	High Similarity	NPC101996
0.9107	High Similarity	NPC97523
0.9103	High Similarity	NPC62042
0.9103	High Similarity	NPC230713
0.9103	High Similarity	NPC78335
0.9097	High Similarity	NPC194856
0.9096	High Similarity	NPC227906
0.9091	High Similarity	NPC230619
0.9091	High Similarity	NPC54098
0.9085	High Similarity	NPC152477
0.9085	High Similarity	NPC211309
0.9085	High Similarity	NPC288813
0.9085	High Similarity	NPC247136
0.908	High Similarity	NPC128293
0.908	High Similarity	NPC173292
0.9074	High Similarity	NPC270837
0.9074	High Similarity	NPC197168
0.9074	High Similarity	NPC236521
0.9074	High Similarity	NPC152659
0.9074	High Similarity	NPC248638
0.9074	High Similarity	NPC236132
0.9074	High Similarity	NPC220313
0.9068	High Similarity	NPC258331
0.9068	High Similarity	NPC474351
0.9068	High Similarity	NPC475883
0.9068	High Similarity	NPC474186
0.9068	High Similarity	NPC474187
0.9068	High Similarity	NPC187354
0.9068	High Similarity	NPC29876

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 NPC37183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	955
0.2-0.3	1744
0.3-0.4	2636
0.4-0.5	1874
0.5-0.6	1003
0.6-0.7	387
0.7-0.8	127
0.8-0.85	40
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD2801	Approved
0.8889	High Similarity	NPD5494	Approved
0.8868	High Similarity	NPD1934	Approved
0.882	High Similarity	NPD3882	Suspended
0.8599	High Similarity	NPD1511	Approved
0.8589	High Similarity	NPD4868	Clinical (unspecified phase)
0.8571	High Similarity	NPD3818	Discontinued
0.8563	High Similarity	NPD6168	Clinical (unspecified phase)
0.8563	High Similarity	NPD6166	Phase 2
0.8563	High Similarity	NPD6167	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD1247	Approved
0.8491	Intermediate Similarity	NPD1512	Approved
0.848	Intermediate Similarity	NPD6559	Discontinued
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8383	Intermediate Similarity	NPD6959	Discontinued
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD3749	Approved
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.8284	Intermediate Similarity	NPD3926	Phase 2
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8218	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7054	Approved
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8155	Intermediate Similarity	NPD919	Approved
0.815	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2800	Approved
0.8103	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6797	Phase 2
0.8101	Intermediate Similarity	NPD2344	Approved
0.8098	Intermediate Similarity	NPD920	Approved
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8086	Intermediate Similarity	NPD2532	Approved
0.8086	Intermediate Similarity	NPD2533	Approved
0.8086	Intermediate Similarity	NPD2534	Approved
0.8057	Intermediate Similarity	NPD7251	Discontinued
0.8038	Intermediate Similarity	NPD2796	Approved
0.8036	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD1243	Approved
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6801	Discontinued
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7925	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD6799	Approved
0.791	Intermediate Similarity	NPD7808	Phase 3
0.7901	Intermediate Similarity	NPD2309	Approved
0.7886	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5402	Approved
0.7853	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.7785	Intermediate Similarity	NPD230	Phase 1
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6234	Discontinued
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3750	Approved
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD7390	Discontinued
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3226	Approved
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD6100	Approved
0.7485	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5403	Approved
0.7442	Intermediate Similarity	NPD37	Approved
0.743	Intermediate Similarity	NPD7228	Approved
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6651	Approved
0.7401	Intermediate Similarity	NPD3787	Discontinued
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8313	Approved
0.7377	Intermediate Similarity	NPD8312	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2313	Discontinued
0.7366	Intermediate Similarity	NPD4287	Approved
0.7358	Intermediate Similarity	NPD4908	Phase 1
0.7356	Intermediate Similarity	NPD2296	Approved
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD5401	Approved
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD3027	Phase 3
0.731	Intermediate Similarity	NPD1653	Approved
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6776	Approved
0.7292	Intermediate Similarity	NPD6781	Approved
0.7292	Intermediate Similarity	NPD6777	Approved
0.7292	Intermediate Similarity	NPD6782	Approved
0.7292	Intermediate Similarity	NPD6779	Approved
0.7292	Intermediate Similarity	NPD6778	Approved
0.7292	Intermediate Similarity	NPD6780	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD6279	Approved
0.7241	Intermediate Similarity	NPD6280	Approved
0.7229	Intermediate Similarity	NPD1471	Phase 3
0.7211	Intermediate Similarity	NPD4360	Phase 2
0.7211	Intermediate Similarity	NPD4363	Phase 3
0.7205	Intermediate Similarity	NPD4625	Phase 3
0.72	Intermediate Similarity	NPD5760	Phase 2
0.72	Intermediate Similarity	NPD5761	Phase 2
0.7188	Intermediate Similarity	NPD9494	Approved
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7186	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.7158	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD1933	Approved
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7111	Intermediate Similarity	NPD6808	Phase 2
0.7092	Intermediate Similarity	NPD7698	Approved
0.7092	Intermediate Similarity	NPD7697	Approved
0.7092	Intermediate Similarity	NPD7696	Phase 3
0.7089	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5242	Approved
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7044	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2654	Approved
0.7041	Intermediate Similarity	NPD6823	Phase 2
0.7039	Intermediate Similarity	NPD7907	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7035	Intermediate Similarity	NPD7701	Phase 2
0.7033	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6534	Approved
0.7031	Intermediate Similarity	NPD6535	Approved
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4111	Phase 1
0.7024	Intermediate Similarity	NPD4665	Approved
0.7019	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.6989	Remote Similarity	NPD7240	Approved
0.6985	Remote Similarity	NPD7584	Approved
0.6982	Remote Similarity	NPD2424	Discontinued
0.6971	Remote Similarity	NPD7458	Discontinued
0.6966	Remote Similarity	NPD5353	Approved
0.6965	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7874	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