NPASS Compound

Structure

CID211565 OpenBabel06191716002D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.5731 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 20 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 10 2 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	4.779
LogD:	3.531
LogS:	-3.956
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.816
Synthetic Accessibility Score:	2.504
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.683
MDCK Permeability:	2.4919549105106853e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.293
Plasma Protein Binding (PPB):	98.7150650024414%
Volume Distribution (VD):	0.459
Pgp-substrate:	1.5155328512191772%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.463
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.343
CYP2D6-substrate:	0.534
CYP3A4-inhibitor:	0.352
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	8.145
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.192
Skin Sensitization:	0.397
Carcinogencity:	0.533
Eye Corrosion:	0.003
Eye Irritation:	0.133
Respiratory Toxicity:	0.655

Download Data

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

Natural Product: NPC211565

Natural Product ID:	NPC211565
*Common Name:**	Dihydromollugin
IUPAC Name:	methyl 6-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate
Synonyms:	Dihydromollugin
Standard InCHIKey:	AKPYYGWMASCNAF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-7,18H,8-9H2,1-3H3
SMILES:	COC(=O)c1c2CCC(Oc2c2c(c1O)cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459117
PubChem CID:	10779560
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2784	Radix rubiae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	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	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	2.0	ug.mL-1	PMID[505110]
NPT27	Others	Unspecified		CC50	=	8.2	ug.mL-1	PMID[505110]

☑ 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 NPC211565 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	346
0.1-0.2	1589
0.2-0.3	3659
0.3-0.4	9277
0.4-0.5	9417
0.5-0.6	3923
0.6-0.7	7157
0.7-0.8	6737
0.8-0.85	533
0.85-0.9	50
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC60389
0.9388	High Similarity	NPC477691
0.932	High Similarity	NPC477690
0.9013	High Similarity	NPC477692
0.8933	High Similarity	NPC281272
0.8933	High Similarity	NPC217447
0.8903	High Similarity	NPC477689
0.8897	High Similarity	NPC329493
0.8874	High Similarity	NPC135522
0.8859	High Similarity	NPC70764
0.8824	High Similarity	NPC67197
0.8808	High Similarity	NPC175978
0.8742	High Similarity	NPC39819
0.8725	High Similarity	NPC71055
0.8701	High Similarity	NPC44199
0.8699	High Similarity	NPC124365
0.8693	High Similarity	NPC3898
0.8675	High Similarity	NPC227122
0.8667	High Similarity	NPC5537
0.8662	High Similarity	NPC17432
0.8658	High Similarity	NPC300540
0.8645	High Similarity	NPC474373
0.8645	High Similarity	NPC186113
0.8636	High Similarity	NPC146211
0.8636	High Similarity	NPC472453
0.8627	High Similarity	NPC178964
0.8627	High Similarity	NPC280530
0.8627	High Similarity	NPC95842
0.8611	High Similarity	NPC115861
0.8609	High Similarity	NPC233267
0.8609	High Similarity	NPC291049
0.8599	High Similarity	NPC473961
0.8592	High Similarity	NPC118253
0.859	High Similarity	NPC143050
0.8582	High Similarity	NPC31539
0.8571	High Similarity	NPC149780
0.8562	High Similarity	NPC273483
0.8553	High Similarity	NPC150928
0.8552	High Similarity	NPC471542
0.8543	High Similarity	NPC37139
0.8543	High Similarity	NPC105415
0.8542	High Similarity	NPC22222
0.8542	High Similarity	NPC281513
0.8535	High Similarity	NPC24761
0.8533	High Similarity	NPC163846
0.8533	High Similarity	NPC301949
0.8533	High Similarity	NPC225173
0.8523	High Similarity	NPC274085
0.8523	High Similarity	NPC89664
0.8521	High Similarity	NPC141549
0.8509	High Similarity	NPC241874
0.8506	High Similarity	NPC329844
0.8506	High Similarity	NPC210942
0.8506	High Similarity	NPC472799
0.8506	High Similarity	NPC169990
0.85	High Similarity	NPC76647
0.8497	Intermediate Similarity	NPC72958
0.8497	Intermediate Similarity	NPC149526
0.8497	Intermediate Similarity	NPC232645
0.8497	Intermediate Similarity	NPC474417
0.8497	Intermediate Similarity	NPC133856
0.8489	Intermediate Similarity	NPC320847
0.8487	Intermediate Similarity	NPC100985
0.8487	Intermediate Similarity	NPC158338
0.8487	Intermediate Similarity	NPC97028
0.8487	Intermediate Similarity	NPC65589
0.8487	Intermediate Similarity	NPC288036
0.8487	Intermediate Similarity	NPC97029
0.8487	Intermediate Similarity	NPC266499
0.8477	Intermediate Similarity	NPC125801
0.8472	Intermediate Similarity	NPC27394
0.8471	Intermediate Similarity	NPC47623
0.8467	Intermediate Similarity	NPC478019
0.8467	Intermediate Similarity	NPC473951
0.8456	Intermediate Similarity	NPC163948
0.8456	Intermediate Similarity	NPC476473
0.8452	Intermediate Similarity	NPC55662
0.8452	Intermediate Similarity	NPC166054
0.8451	Intermediate Similarity	NPC278787
0.8446	Intermediate Similarity	NPC145673
0.8442	Intermediate Similarity	NPC271681
0.8442	Intermediate Similarity	NPC87708
0.8442	Intermediate Similarity	NPC474843
0.8438	Intermediate Similarity	NPC30027
0.8435	Intermediate Similarity	NPC1268
0.8431	Intermediate Similarity	NPC325983
0.8431	Intermediate Similarity	NPC202595
0.8431	Intermediate Similarity	NPC119929
0.8431	Intermediate Similarity	NPC470107
0.8431	Intermediate Similarity	NPC158866
0.8428	Intermediate Similarity	NPC207690
0.8428	Intermediate Similarity	NPC474350
0.8428	Intermediate Similarity	NPC197168
0.8421	Intermediate Similarity	NPC256672
0.8421	Intermediate Similarity	NPC55327
0.8421	Intermediate Similarity	NPC186397
0.8421	Intermediate Similarity	NPC27221
0.8421	Intermediate Similarity	NPC37135
0.8421	Intermediate Similarity	NPC7025
0.8418	Intermediate Similarity	NPC66288
0.8411	Intermediate Similarity	NPC308799
0.8411	Intermediate Similarity	NPC267509
0.8403	Intermediate Similarity	NPC472591
0.84	Intermediate Similarity	NPC306816
0.84	Intermediate Similarity	NPC260152
0.8397	Intermediate Similarity	NPC474360
0.8397	Intermediate Similarity	NPC4547
0.8395	Intermediate Similarity	NPC313304
0.8389	Intermediate Similarity	NPC69755
0.8389	Intermediate Similarity	NPC474300
0.8385	Intermediate Similarity	NPC234331
0.8385	Intermediate Similarity	NPC225419
0.8378	Intermediate Similarity	NPC168471
0.8377	Intermediate Similarity	NPC478148
0.8375	Intermediate Similarity	NPC25361
0.8375	Intermediate Similarity	NPC178281
0.8369	Intermediate Similarity	NPC71525
0.8366	Intermediate Similarity	NPC329933
0.8366	Intermediate Similarity	NPC223988
0.8366	Intermediate Similarity	NPC65775
0.8366	Intermediate Similarity	NPC10027
0.8365	Intermediate Similarity	NPC216752
0.8365	Intermediate Similarity	NPC144843
0.8365	Intermediate Similarity	NPC229632
0.8355	Intermediate Similarity	NPC22005
0.8355	Intermediate Similarity	NPC123202
0.8355	Intermediate Similarity	NPC34802
0.8355	Intermediate Similarity	NPC61284
0.8355	Intermediate Similarity	NPC7943
0.8355	Intermediate Similarity	NPC113428
0.8354	Intermediate Similarity	NPC119224
0.8354	Intermediate Similarity	NPC289147
0.8354	Intermediate Similarity	NPC199533
0.8354	Intermediate Similarity	NPC470454
0.8345	Intermediate Similarity	NPC274876
0.8344	Intermediate Similarity	NPC134621
0.8344	Intermediate Similarity	NPC32470
0.8344	Intermediate Similarity	NPC246647
0.8344	Intermediate Similarity	NPC165977
0.8344	Intermediate Similarity	NPC217677
0.8344	Intermediate Similarity	NPC96342
0.8344	Intermediate Similarity	NPC47152
0.8344	Intermediate Similarity	NPC212967
0.8344	Intermediate Similarity	NPC263483
0.8344	Intermediate Similarity	NPC164110
0.8333	Intermediate Similarity	NPC99613
0.8333	Intermediate Similarity	NPC470160
0.8333	Intermediate Similarity	NPC66029
0.8333	Intermediate Similarity	NPC66593
0.8333	Intermediate Similarity	NPC49487
0.8333	Intermediate Similarity	NPC149618
0.8333	Intermediate Similarity	NPC89625
0.8323	Intermediate Similarity	NPC24232
0.8323	Intermediate Similarity	NPC37870
0.8323	Intermediate Similarity	NPC154683
0.8323	Intermediate Similarity	NPC178173
0.8323	Intermediate Similarity	NPC29160
0.8323	Intermediate Similarity	NPC40356
0.8323	Intermediate Similarity	NPC473967
0.8322	Intermediate Similarity	NPC257003
0.8322	Intermediate Similarity	NPC7569
0.8313	Intermediate Similarity	NPC236132
0.8313	Intermediate Similarity	NPC156082
0.8313	Intermediate Similarity	NPC270837
0.8312	Intermediate Similarity	NPC294646
0.8312	Intermediate Similarity	NPC120105
0.8312	Intermediate Similarity	NPC101957
0.8312	Intermediate Similarity	NPC295036
0.8311	Intermediate Similarity	NPC18457
0.8303	Intermediate Similarity	NPC312630
0.8303	Intermediate Similarity	NPC324220
0.8302	Intermediate Similarity	NPC32694
0.8302	Intermediate Similarity	NPC474187
0.8302	Intermediate Similarity	NPC61010
0.8301	Intermediate Similarity	NPC172329
0.8301	Intermediate Similarity	NPC2569
0.8301	Intermediate Similarity	NPC474107
0.8289	Intermediate Similarity	NPC237208
0.8289	Intermediate Similarity	NPC473927
0.8289	Intermediate Similarity	NPC469758
0.8289	Intermediate Similarity	NPC196114
0.8286	Intermediate Similarity	NPC61685
0.8286	Intermediate Similarity	NPC236189
0.8282	Intermediate Similarity	NPC477572
0.8282	Intermediate Similarity	NPC124470
0.8282	Intermediate Similarity	NPC109827
0.8282	Intermediate Similarity	NPC474004
0.8282	Intermediate Similarity	NPC477571
0.8282	Intermediate Similarity	NPC477573
0.828	Intermediate Similarity	NPC180924
0.828	Intermediate Similarity	NPC142339
0.828	Intermediate Similarity	NPC469507
0.8278	Intermediate Similarity	NPC95123
0.8278	Intermediate Similarity	NPC471305
0.8278	Intermediate Similarity	NPC66404
0.8276	Intermediate Similarity	NPC287533
0.8272	Intermediate Similarity	NPC473094
0.8269	Intermediate Similarity	NPC474621
0.8269	Intermediate Similarity	NPC475770
0.8269	Intermediate Similarity	NPC474622

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 NPC211565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	985
0.2-0.3	1433
0.3-0.4	2471
0.4-0.5	2054
0.5-0.6	1231
0.6-0.7	469
0.7-0.8	168
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD2346	Discontinued
0.8811	High Similarity	NPD2935	Discontinued
0.8487	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD3226	Approved
0.8451	Intermediate Similarity	NPD2313	Discontinued
0.8269	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD6232	Discontinued
0.8231	Intermediate Similarity	NPD2799	Discontinued
0.8224	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD2532	Approved
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8108	Intermediate Similarity	NPD4308	Phase 3
0.8099	Intermediate Similarity	NPD1203	Approved
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8054	Intermediate Similarity	NPD5405	Approved
0.8054	Intermediate Similarity	NPD5406	Approved
0.8054	Intermediate Similarity	NPD5404	Approved
0.8054	Intermediate Similarity	NPD5408	Approved
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD2797	Approved
0.7961	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7003	Approved
0.7945	Intermediate Similarity	NPD411	Approved
0.7943	Intermediate Similarity	NPD1611	Approved
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7933	Intermediate Similarity	NPD1551	Phase 2
0.7931	Intermediate Similarity	NPD6832	Phase 2
0.7925	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD447	Suspended
0.7905	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1283	Approved
0.7888	Intermediate Similarity	NPD3749	Approved
0.7887	Intermediate Similarity	NPD9717	Approved
0.7881	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.787	Intermediate Similarity	NPD8313	Approved
0.787	Intermediate Similarity	NPD8312	Approved
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3750	Approved
0.7838	Intermediate Similarity	NPD4307	Phase 2
0.7829	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3268	Approved
0.7812	Intermediate Similarity	NPD2801	Approved
0.7799	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7764	Intermediate Similarity	NPD5402	Approved
0.7756	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD2979	Phase 3
0.7711	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5710	Approved
0.7697	Intermediate Similarity	NPD5711	Approved
0.7692	Intermediate Similarity	NPD1281	Approved
0.7676	Intermediate Similarity	NPD4626	Approved
0.7671	Intermediate Similarity	NPD2798	Approved
0.7667	Intermediate Similarity	NPD1933	Approved
0.7662	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2344	Approved
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1934	Approved
0.7603	Intermediate Similarity	NPD1470	Approved
0.76	Intermediate Similarity	NPD4060	Phase 1
0.7597	Intermediate Similarity	NPD1549	Phase 2
0.7595	Intermediate Similarity	NPD6273	Approved
0.7584	Intermediate Similarity	NPD7985	Registered
0.7582	Intermediate Similarity	NPD6099	Approved
0.7582	Intermediate Similarity	NPD6100	Approved
0.7576	Intermediate Similarity	NPD5494	Approved
0.7569	Intermediate Similarity	NPD1201	Approved
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1398	Phase 1
0.7531	Intermediate Similarity	NPD6844	Discontinued
0.7529	Intermediate Similarity	NPD8150	Discontinued
0.7518	Intermediate Similarity	NPD9493	Approved
0.7518	Intermediate Similarity	NPD7340	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD5691	Approved
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7483	Intermediate Similarity	NPD1651	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7468	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD1511	Approved
0.7468	Intermediate Similarity	NPD2438	Suspended
0.7468	Intermediate Similarity	NPD4476	Approved
0.7468	Intermediate Similarity	NPD4477	Approved
0.7467	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD7644	Approved
0.7452	Intermediate Similarity	NPD2309	Approved
0.7447	Intermediate Similarity	NPD6671	Approved
0.7439	Intermediate Similarity	NPD3817	Phase 2
0.7436	Intermediate Similarity	NPD2800	Approved
0.7433	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7783	Phase 2
0.7432	Intermediate Similarity	NPD7435	Discontinued
0.7432	Intermediate Similarity	NPD1019	Discontinued
0.7423	Intermediate Similarity	NPD6801	Discontinued
0.7421	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6585	Discontinued
0.7403	Intermediate Similarity	NPD7033	Discontinued
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.7399	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1481	Phase 2
0.7397	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1512	Approved
0.7368	Intermediate Similarity	NPD1240	Approved
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD5890	Approved
0.7362	Intermediate Similarity	NPD5889	Approved
0.7358	Intermediate Similarity	NPD6799	Approved
0.7355	Intermediate Similarity	NPD2796	Approved
0.7355	Intermediate Similarity	NPD2531	Phase 2
0.7349	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7329	Intermediate Similarity	NPD920	Approved
0.7329	Intermediate Similarity	NPD5403	Approved
0.7329	Intermediate Similarity	NPD1535	Discovery
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7303	Intermediate Similarity	NPD6233	Phase 2
0.7297	Intermediate Similarity	NPD6696	Suspended
0.7297	Intermediate Similarity	NPD3225	Approved
0.7294	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6166	Phase 2
0.7294	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7698	Approved
0.7243	Intermediate Similarity	NPD7696	Phase 3
0.7243	Intermediate Similarity	NPD7697	Approved
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7234	Intermediate Similarity	NPD7635	Approved
0.723	Intermediate Similarity	NPD4749	Approved
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD1243	Approved
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7209	Intermediate Similarity	NPD3818	Discontinued
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD4618	Approved
0.7208	Intermediate Similarity	NPD4622	Approved
0.7205	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5401	Approved
0.7204	Intermediate Similarity	NPD7870	Phase 2
0.7204	Intermediate Similarity	NPD7871	Phase 2
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7874	Approved
0.7196	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD17	Approved
0.7192	Intermediate Similarity	NPD1778	Approved
0.719	Intermediate Similarity	NPD8032	Phase 2
0.7184	Intermediate Similarity	NPD5953	Discontinued
0.7182	Intermediate Similarity	NPD6534	Approved
0.7182	Intermediate Similarity	NPD6535	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7171	Intermediate Similarity	NPD7008	Discontinued
0.7171	Intermediate Similarity	NPD7095	Approved
0.717	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7286	Phase 2
0.7168	Intermediate Similarity	NPD7054	Approved
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2897	Discontinued
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7133	Intermediate Similarity	NPD5951	Approved
0.7127	Intermediate Similarity	NPD6213	Phase 3

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