NPASS Compound

Structure

NPC49272 OpenBabel07101718232D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.6092 2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5602 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2183 -0.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2238 -0.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 18 22 1 6 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	339.592
LogP:	2.941
LogD:	1.524
LogS:	-3.204
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.861
Synthetic Accessibility Score:	4.423
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.761
MDCK Permeability:	2.6660190997063182e-05
Pgp-inhibitor:	0.794
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917
Plasma Protein Binding (PPB):	79.53775024414062%
Volume Distribution (VD):	0.925
Pgp-substrate:	12.882752418518066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.687
CYP2C19-inhibitor:	0.459
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.323
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.801

ADMET: Excretion

Clearance (CL):	6.828
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.47
Carcinogencity:	0.63
Eye Corrosion:	0.015
Eye Irritation:	0.039
Respiratory Toxicity:	0.594

Download Data

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

Natural Product: NPC49272

Natural Product ID:	NPC49272
*Common Name:**	Distachyasin
IUPAC Name:	(4bR,5R,9aR,10aS)-5,9a-dihydroxy-7-methoxy-11,11-dimethyl-4b,5,10,10a-tetrahydrobenzo[b]fluoren-9-one
Synonyms:	Distachyasin
Standard InCHIKey:	VZQCDBNQPVXLLR-TXJVSEOTSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-19(2)13-7-5-4-6-12(13)17-15(19)10-20(23)14(18(17)22)8-11(24-3)9-16(20)21/h4-9,15,17-18,22-23H,10H2,1-3H3/t15-,17-,18-,20+/m0/s1
SMILES:	COC1=CC(=O)[C@@]2(C(=C1)[C@H](O)[C@@H]1[C@H](C2)C(c2c1cccc2)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218266
PubChem CID:	16066853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO28619	Carex distachya	Species	Cyperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16971124]
NPO28619	Carex distachya	Species	Cyperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17112723]
NPO28619	Carex distachya	Species	Cyperaceae	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
Others	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	60.0	%	PMID[547801]
NPT2	Others	Unspecified	Activity	=	32.0	%	PMID[547801]
NPT2	Others	Unspecified	Activity	=	39.0	%	PMID[547801]
NPT2	Others	Unspecified	Activity	=	10.7	%	PMID[547801]
NPT2	Others	Unspecified	Inhibition	=	59.0	%	PMID[547801]

☑ 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 NPC49272 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	257
0.1-0.2	1050
0.2-0.3	2112
0.3-0.4	4633
0.4-0.5	9138
0.5-0.6	14159
0.6-0.7	10354
0.7-0.8	988
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.837	Intermediate Similarity	NPC310662
0.8175	Intermediate Similarity	NPC212207
0.8175	Intermediate Similarity	NPC23894
0.8175	Intermediate Similarity	NPC474659
0.8102	Intermediate Similarity	NPC203486
0.8088	Intermediate Similarity	NPC80599
0.8042	Intermediate Similarity	NPC471162
0.8	Intermediate Similarity	NPC471189
0.7986	Intermediate Similarity	NPC309056
0.7985	Intermediate Similarity	NPC253681
0.7969	Intermediate Similarity	NPC472862
0.7958	Intermediate Similarity	NPC140021
0.7941	Intermediate Similarity	NPC472388
0.7929	Intermediate Similarity	NPC39549
0.7929	Intermediate Similarity	NPC243893
0.7929	Intermediate Similarity	NPC262324
0.7926	Intermediate Similarity	NPC478165
0.7926	Intermediate Similarity	NPC478162
0.7914	Intermediate Similarity	NPC471864
0.7899	Intermediate Similarity	NPC15850
0.7895	Intermediate Similarity	NPC140118
0.7895	Intermediate Similarity	NPC12881
0.7883	Intermediate Similarity	NPC72915
0.7879	Intermediate Similarity	NPC293831
0.7879	Intermediate Similarity	NPC369
0.7868	Intermediate Similarity	NPC225103
0.7857	Intermediate Similarity	NPC472551
0.7857	Intermediate Similarity	NPC472545
0.7842	Intermediate Similarity	NPC48929
0.7832	Intermediate Similarity	NPC472546
0.7829	Intermediate Similarity	NPC470820
0.7817	Intermediate Similarity	NPC472547
0.7817	Intermediate Similarity	NPC79921
0.781	Intermediate Similarity	NPC473443
0.7803	Intermediate Similarity	NPC472981
0.7794	Intermediate Similarity	NPC262936
0.7794	Intermediate Similarity	NPC30491
0.7794	Intermediate Similarity	NPC195224
0.7793	Intermediate Similarity	NPC301946
0.7793	Intermediate Similarity	NPC277053
0.7786	Intermediate Similarity	NPC476645
0.7778	Intermediate Similarity	NPC470816
0.777	Intermediate Similarity	NPC101043
0.777	Intermediate Similarity	NPC306799
0.777	Intermediate Similarity	NPC165612
0.7769	Intermediate Similarity	NPC80605
0.7769	Intermediate Similarity	NPC323440
0.7769	Intermediate Similarity	NPC222968
0.7737	Intermediate Similarity	NPC93632
0.7733	Intermediate Similarity	NPC471176
0.7727	Intermediate Similarity	NPC133389
0.7727	Intermediate Similarity	NPC183339
0.7727	Intermediate Similarity	NPC234337
0.7724	Intermediate Similarity	NPC80895
0.7724	Intermediate Similarity	NPC471912
0.7721	Intermediate Similarity	NPC477365
0.7721	Intermediate Similarity	NPC5486
0.7721	Intermediate Similarity	NPC169913
0.7718	Intermediate Similarity	NPC145649
0.7718	Intermediate Similarity	NPC22571
0.7718	Intermediate Similarity	NPC138641
0.7718	Intermediate Similarity	NPC233581
0.7718	Intermediate Similarity	NPC283875
0.7718	Intermediate Similarity	NPC469648
0.7718	Intermediate Similarity	NPC469647
0.7717	Intermediate Similarity	NPC471188
0.7714	Intermediate Similarity	NPC329913
0.7714	Intermediate Similarity	NPC126516
0.7708	Intermediate Similarity	NPC63737
0.7708	Intermediate Similarity	NPC183540
0.7708	Intermediate Similarity	NPC182869
0.7703	Intermediate Similarity	NPC125033
0.7698	Intermediate Similarity	NPC209851
0.7692	Intermediate Similarity	NPC473440
0.7692	Intermediate Similarity	NPC275592
0.7692	Intermediate Similarity	NPC161151
0.7692	Intermediate Similarity	NPC90614
0.7692	Intermediate Similarity	NPC100913
0.7687	Intermediate Similarity	NPC132652
0.7687	Intermediate Similarity	NPC65627
0.7681	Intermediate Similarity	NPC147561
0.7681	Intermediate Similarity	NPC475138
0.7671	Intermediate Similarity	NPC478264
0.7671	Intermediate Similarity	NPC3732
0.7671	Intermediate Similarity	NPC127857
0.7671	Intermediate Similarity	NPC478164
0.7667	Intermediate Similarity	NPC11588
0.7667	Intermediate Similarity	NPC134685
0.7667	Intermediate Similarity	NPC229545
0.7667	Intermediate Similarity	NPC248265
0.7664	Intermediate Similarity	NPC477370
0.7661	Intermediate Similarity	NPC474307
0.7655	Intermediate Similarity	NPC477894
0.7655	Intermediate Similarity	NPC91703
0.7655	Intermediate Similarity	NPC95449
0.7652	Intermediate Similarity	NPC204784
0.7651	Intermediate Similarity	NPC471103
0.7651	Intermediate Similarity	NPC472398
0.7647	Intermediate Similarity	NPC470649
0.7647	Intermediate Similarity	NPC87985
0.7647	Intermediate Similarity	NPC470818
0.7647	Intermediate Similarity	NPC275576
0.7647	Intermediate Similarity	NPC477366
0.7647	Intermediate Similarity	NPC478107
0.7647	Intermediate Similarity	NPC236405
0.7647	Intermediate Similarity	NPC45821
0.7642	Intermediate Similarity	NPC247957
0.7642	Intermediate Similarity	NPC249187
0.7639	Intermediate Similarity	NPC118080
0.7639	Intermediate Similarity	NPC41481
0.7639	Intermediate Similarity	NPC224491
0.7639	Intermediate Similarity	NPC472576
0.7639	Intermediate Similarity	NPC27377
0.7639	Intermediate Similarity	NPC291599
0.7639	Intermediate Similarity	NPC97947
0.7639	Intermediate Similarity	NPC87448
0.7635	Intermediate Similarity	NPC60509
0.7635	Intermediate Similarity	NPC472938
0.7635	Intermediate Similarity	NPC473215
0.7635	Intermediate Similarity	NPC250046
0.7635	Intermediate Similarity	NPC81698
0.7635	Intermediate Similarity	NPC472936
0.7635	Intermediate Similarity	NPC472937
0.763	Intermediate Similarity	NPC77691
0.763	Intermediate Similarity	NPC469742
0.7626	Intermediate Similarity	NPC472418
0.7622	Intermediate Similarity	NPC9905
0.7619	Intermediate Similarity	NPC478263
0.7619	Intermediate Similarity	NPC475552
0.7619	Intermediate Similarity	NPC473602
0.7616	Intermediate Similarity	NPC473670
0.7616	Intermediate Similarity	NPC114357
0.7616	Intermediate Similarity	NPC469730
0.7616	Intermediate Similarity	NPC155329
0.7616	Intermediate Similarity	NPC132599
0.7616	Intermediate Similarity	NPC473632
0.7616	Intermediate Similarity	NPC259144
0.7616	Intermediate Similarity	NPC21410
0.7606	Intermediate Similarity	NPC472372
0.7606	Intermediate Similarity	NPC472374
0.7603	Intermediate Similarity	NPC38696
0.7594	Intermediate Similarity	NPC133302
0.7594	Intermediate Similarity	NPC238861
0.7594	Intermediate Similarity	NPC77000
0.7591	Intermediate Similarity	NPC81135
0.7586	Intermediate Similarity	NPC136649
0.7586	Intermediate Similarity	NPC34012
0.7586	Intermediate Similarity	NPC192658
0.7584	Intermediate Similarity	NPC52161
0.7584	Intermediate Similarity	NPC473214
0.7584	Intermediate Similarity	NPC162751
0.7584	Intermediate Similarity	NPC470245
0.7584	Intermediate Similarity	NPC7095
0.7584	Intermediate Similarity	NPC475561
0.7584	Intermediate Similarity	NPC475417
0.7584	Intermediate Similarity	NPC478163
0.7584	Intermediate Similarity	NPC161239
0.7584	Intermediate Similarity	NPC198455
0.7584	Intermediate Similarity	NPC476173
0.7584	Intermediate Similarity	NPC165260
0.7576	Intermediate Similarity	NPC318173
0.7574	Intermediate Similarity	NPC471758
0.7574	Intermediate Similarity	NPC295664
0.7571	Intermediate Similarity	NPC476976
0.7571	Intermediate Similarity	NPC476847
0.7569	Intermediate Similarity	NPC234548
0.7569	Intermediate Similarity	NPC248287
0.7569	Intermediate Similarity	NPC97667
0.7569	Intermediate Similarity	NPC171207
0.7569	Intermediate Similarity	NPC87934
0.7569	Intermediate Similarity	NPC476643
0.7569	Intermediate Similarity	NPC162613
0.7568	Intermediate Similarity	NPC217918
0.7568	Intermediate Similarity	NPC478160
0.7566	Intermediate Similarity	NPC11410
0.7556	Intermediate Similarity	NPC273336
0.7556	Intermediate Similarity	NPC182333
0.7554	Intermediate Similarity	NPC131684
0.7554	Intermediate Similarity	NPC262819
0.7552	Intermediate Similarity	NPC475373
0.7551	Intermediate Similarity	NPC472556
0.7551	Intermediate Similarity	NPC477207
0.755	Intermediate Similarity	NPC219419
0.7548	Intermediate Similarity	NPC475536
0.7548	Intermediate Similarity	NPC165234
0.754	Intermediate Similarity	NPC472980
0.7538	Intermediate Similarity	NPC93181
0.7536	Intermediate Similarity	NPC230331
0.7535	Intermediate Similarity	NPC477893
0.7535	Intermediate Similarity	NPC194970
0.7535	Intermediate Similarity	NPC477896
0.7534	Intermediate Similarity	NPC163087
0.7533	Intermediate Similarity	NPC470153
0.7533	Intermediate Similarity	NPC106524
0.7533	Intermediate Similarity	NPC51602
0.7533	Intermediate Similarity	NPC290695
0.7533	Intermediate Similarity	NPC197037
0.7533	Intermediate Similarity	NPC253591
0.752	Intermediate Similarity	NPC257353
0.752	Intermediate Similarity	NPC471186

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 NPC49272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	752
0.2-0.3	1324
0.3-0.4	2772
0.4-0.5	2268
0.5-0.6	1391
0.6-0.7	397
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7917	Intermediate Similarity	NPD7236	Approved
0.771	Intermediate Similarity	NPD7741	Discontinued
0.7651	Intermediate Similarity	NPD7239	Suspended
0.7594	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD2932	Approved
0.7463	Intermediate Similarity	NPD3019	Approved
0.7407	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7961	Discontinued
0.7308	Intermediate Similarity	NPD7058	Phase 2
0.7308	Intermediate Similarity	NPD7057	Phase 3
0.7273	Intermediate Similarity	NPD2629	Approved
0.7252	Intermediate Similarity	NPD6858	Approved
0.7252	Intermediate Similarity	NPD7094	Approved
0.7239	Intermediate Similarity	NPD7610	Discontinued
0.7231	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6663	Approved
0.7163	Intermediate Similarity	NPD5736	Approved
0.7153	Intermediate Similarity	NPD3026	Approved
0.7153	Intermediate Similarity	NPD3023	Approved
0.7132	Intermediate Similarity	NPD3025	Approved
0.7132	Intermediate Similarity	NPD3024	Approved
0.7117	Intermediate Similarity	NPD7799	Discontinued
0.7075	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3091	Approved
0.7059	Intermediate Similarity	NPD7009	Phase 2
0.7059	Intermediate Similarity	NPD6273	Approved
0.7031	Intermediate Similarity	NPD5909	Discontinued
0.7023	Intermediate Similarity	NPD2067	Discontinued
0.7021	Intermediate Similarity	NPD3094	Phase 2
0.6993	Remote Similarity	NPD7055	Discontinued
0.6987	Remote Similarity	NPD7028	Phase 2
0.698	Remote Similarity	NPD5762	Approved
0.698	Remote Similarity	NPD5763	Approved
0.6978	Remote Similarity	NPD3092	Approved
0.6963	Remote Similarity	NPD4198	Discontinued
0.6962	Remote Similarity	NPD5761	Phase 2
0.6962	Remote Similarity	NPD5760	Phase 2
0.6957	Remote Similarity	NPD3095	Discontinued
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8166	Discontinued
0.6944	Remote Similarity	NPD7008	Discontinued
0.6941	Remote Similarity	NPD8434	Phase 2
0.6918	Remote Similarity	NPD4140	Approved
0.6917	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8127	Discontinued
0.6913	Remote Similarity	NPD6100	Approved
0.6913	Remote Similarity	NPD6099	Approved
0.6899	Remote Similarity	NPD1237	Approved
0.6899	Remote Similarity	NPD37	Approved
0.6889	Remote Similarity	NPD5951	Approved
0.6883	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5211	Phase 2
0.6853	Remote Similarity	NPD4624	Approved
0.6853	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6085	Phase 2
0.6849	Remote Similarity	NPD8032	Phase 2
0.6846	Remote Similarity	NPD7305	Phase 1
0.6838	Remote Similarity	NPD3317	Approved
0.6831	Remote Similarity	NPD1876	Approved
0.6822	Remote Similarity	NPD6647	Phase 2
0.6815	Remote Similarity	NPD6010	Discontinued
0.6806	Remote Similarity	NPD7084	Phase 3
0.6803	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6685	Approved
0.6783	Remote Similarity	NPD1470	Approved
0.6781	Remote Similarity	NPD3764	Approved
0.677	Remote Similarity	NPD4965	Approved
0.677	Remote Similarity	NPD4966	Approved
0.677	Remote Similarity	NPD4967	Phase 2
0.6769	Remote Similarity	NPD5141	Approved
0.6765	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5735	Approved
0.6757	Remote Similarity	NPD6355	Discontinued
0.6755	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6004	Phase 3
0.6755	Remote Similarity	NPD6002	Phase 3
0.6755	Remote Similarity	NPD6005	Phase 3
0.6746	Remote Similarity	NPD6765	Approved
0.6746	Remote Similarity	NPD6764	Approved
0.6746	Remote Similarity	NPD8368	Discontinued
0.6738	Remote Similarity	NPD1201	Approved
0.6736	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4628	Phase 3
0.6732	Remote Similarity	NPD7003	Approved
0.6725	Remote Similarity	NPD8407	Phase 2
0.672	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4696	Approved
0.6719	Remote Similarity	NPD5286	Approved
0.6719	Remote Similarity	NPD5285	Approved
0.6719	Remote Similarity	NPD2066	Phase 3
0.6718	Remote Similarity	NPD5048	Discontinued
0.6716	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7115	Discovery
0.6714	Remote Similarity	NPD4059	Approved
0.6714	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5126	Approved
0.6714	Remote Similarity	NPD5125	Phase 3
0.6711	Remote Similarity	NPD6353	Approved
0.6693	Remote Similarity	NPD4755	Approved
0.6692	Remote Similarity	NPD5765	Approved
0.6692	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3620	Phase 2
0.6688	Remote Similarity	NPD6190	Approved
0.6688	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5327	Phase 3
0.6643	Remote Similarity	NPD1651	Approved
0.6627	Remote Similarity	NPD4956	Approved
0.6623	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD3750	Approved
0.6623	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5224	Approved
0.6615	Remote Similarity	NPD5226	Approved
0.6615	Remote Similarity	NPD4633	Approved
0.6615	Remote Similarity	NPD5225	Approved
0.6614	Remote Similarity	NPD5221	Approved
0.6614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5222	Approved
0.6614	Remote Similarity	NPD4697	Phase 3
0.6604	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1283	Approved
0.659	Remote Similarity	NPD6785	Approved
0.659	Remote Similarity	NPD6784	Approved
0.6589	Remote Similarity	NPD4700	Approved
0.6585	Remote Similarity	NPD6234	Discontinued
0.6581	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4878	Approved
0.6571	Remote Similarity	NPD8361	Approved
0.6571	Remote Similarity	NPD8360	Approved
0.6565	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1930	Approved
0.6565	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5175	Approved
0.6565	Remote Similarity	NPD1929	Approved
0.6565	Remote Similarity	NPD5174	Approved
0.6562	Remote Similarity	NPD5173	Approved
0.6562	Remote Similarity	NPD3495	Discontinued
0.6561	Remote Similarity	NPD2532	Approved
0.6561	Remote Similarity	NPD2534	Approved
0.6561	Remote Similarity	NPD2533	Approved
0.6557	Remote Similarity	NPD3618	Phase 1
0.6554	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3268	Approved
0.6552	Remote Similarity	NPD2797	Approved
0.655	Remote Similarity	NPD5039	Approved
0.6549	Remote Similarity	NPD4879	Approved
0.6543	Remote Similarity	NPD7819	Suspended
0.6541	Remote Similarity	NPD5697	Approved
0.6538	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD3300	Phase 2
0.6536	Remote Similarity	NPD2346	Discontinued
0.6535	Remote Similarity	NPD1693	Approved
0.6535	Remote Similarity	NPD5210	Approved
0.6535	Remote Similarity	NPD4629	Approved
0.6532	Remote Similarity	NPD4753	Phase 2
0.6527	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4634	Approved
0.6516	Remote Similarity	NPD4110	Phase 3
0.6516	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1510	Phase 2
0.6509	Remote Similarity	NPD3751	Discontinued
0.6506	Remote Similarity	NPD7199	Phase 2
0.6503	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7458	Discontinued
0.6493	Remote Similarity	NPD6881	Approved
0.6493	Remote Similarity	NPD6899	Approved
0.6479	Remote Similarity	NPD4626	Approved
0.6477	Remote Similarity	NPD8435	Approved
0.6474	Remote Similarity	NPD5035	Approved
0.6471	Remote Similarity	NPD5406	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD6650	Approved
0.6471	Remote Similarity	NPD5404	Approved
0.6471	Remote Similarity	NPD5405	Approved
0.6471	Remote Similarity	NPD5408	Approved
0.6467	Remote Similarity	NPD2238	Phase 2
0.6467	Remote Similarity	NPD4060	Phase 1
0.6466	Remote Similarity	NPD6402	Approved
0.6466	Remote Similarity	NPD5739	Approved
0.6466	Remote Similarity	NPD7128	Approved
0.6466	Remote Similarity	NPD6675	Approved
0.6463	Remote Similarity	NPD2861	Phase 2
0.6462	Remote Similarity	NPD7640	Approved
0.6462	Remote Similarity	NPD7639	Approved
0.646	Remote Similarity	NPD6599	Discontinued
0.646	Remote Similarity	NPD4380	Phase 2
0.6458	Remote Similarity	NPD3972	Approved
0.6457	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8150	Discontinued
0.6456	Remote Similarity	NPD7422	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