NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.22
Volume:	443.653
LogP:	4.609
LogD:	3.0
LogS:	-3.755
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	4.423
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051
MDCK Permeability:	2.23786300921347e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	91.02970123291016%
Volume Distribution (VD):	0.467
Pgp-substrate:	6.76740837097168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.849
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	7.723
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.798
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.423
Skin Sensitization:	0.278
Carcinogencity:	0.513
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC477669

Natural Product ID:	NPC477669
*Common Name:**	3-[(5aS,8S,9R,9aR)-11-methoxy-4,5a,9-trimethyl-1-oxo-8-prop-1-en-2-yl-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoic acid
IUPAC Name:	3-[(5aS,8S,9R,9aR)-11-methoxy-4,5a,9-trimethyl-1-oxo-8-prop-1-en-2-yl-3,6,7,8,9a,10-hexahydro-[2]benzofuro[5,6-b]chromen-9-yl]propanoic acid
Synonyms:
Standard InCHIKey:	VVUHSOKZRNWEQD-ISNLERQRSA-N
Standard InCHI:	InChI=1S/C25H32O6/c1-13(2)17-7-10-25(5)18(24(17,4)9-8-19(26)27)11-15-21(31-25)14(3)16-12-30-23(28)20(16)22(15)29-6/h17-18H,1,7-12H2,2-6H3,(H,26,27)/t17-,18+,24+,25-/m0/s1
SMILES:	CC1=C2COC(=O)C2=C(C3=C1O[C@]4(CC[C@H]([C@@]([C@H]4C3)(C)CCC(=O)O)C(=C)C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118706611
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	<	10000	nM	PMID[24852445]
NPT2	Others	Unspecified		IC50	<	10000	nM	PMID[24852445]
NPT2	Others	Unspecified		IC50	=	1000000	nM	PMID[24852445]

☑ 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 NPC477669 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	349
0.1-0.2	1471
0.2-0.3	3023
0.3-0.4	6348
0.4-0.5	10942
0.5-0.6	6430
0.6-0.7	5943
0.7-0.8	7083
0.8-0.85	1007
0.85-0.9	85
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC477674
0.9863	High Similarity	NPC477672
0.9863	High Similarity	NPC477673
0.9664	High Similarity	NPC477671
0.9664	High Similarity	NPC477687
0.96	High Similarity	NPC477675
0.9527	High Similarity	NPC477676
0.9085	High Similarity	NPC472799
0.906	High Similarity	NPC75694
0.9	High Similarity	NPC470357
0.8994	High Similarity	NPC125465
0.8974	High Similarity	NPC239118
0.8968	High Similarity	NPC4547
0.8944	High Similarity	NPC477670
0.894	High Similarity	NPC137296
0.894	High Similarity	NPC8817
0.891	High Similarity	NPC158542
0.8896	High Similarity	NPC217447
0.8896	High Similarity	NPC271681
0.8889	High Similarity	NPC150928
0.8868	High Similarity	NPC100849
0.8854	High Similarity	NPC4950
0.8812	High Similarity	NPC316262
0.8812	High Similarity	NPC314653
0.879	High Similarity	NPC272196
0.8774	High Similarity	NPC273483
0.8766	High Similarity	NPC119929
0.8758	High Similarity	NPC470359
0.8734	High Similarity	NPC474373
0.8734	High Similarity	NPC218818
0.8726	High Similarity	NPC146211
0.8712	High Similarity	NPC477572
0.8712	High Similarity	NPC477571
0.8712	High Similarity	NPC477573
0.871	High Similarity	NPC478148
0.8701	High Similarity	NPC233267
0.8701	High Similarity	NPC291049
0.8693	High Similarity	NPC304351
0.8693	High Similarity	NPC245757
0.8688	High Similarity	NPC473022
0.8679	High Similarity	NPC470810
0.8675	High Similarity	NPC472344
0.8671	High Similarity	NPC196448
0.8654	High Similarity	NPC87708
0.8645	High Similarity	NPC202595
0.8645	High Similarity	NPC158866
0.8642	High Similarity	NPC472621
0.8636	High Similarity	NPC105415
0.8636	High Similarity	NPC37139
0.8631	High Similarity	NPC475656
0.8631	High Similarity	NPC475148
0.8616	High Similarity	NPC472617
0.8614	High Similarity	NPC324220
0.8614	High Similarity	NPC472661
0.8614	High Similarity	NPC312630
0.8599	High Similarity	NPC169990
0.8599	High Similarity	NPC210942
0.8598	High Similarity	NPC315306
0.8598	High Similarity	NPC313717
0.859	High Similarity	NPC474417
0.859	High Similarity	NPC232645
0.859	High Similarity	NPC473131
0.859	High Similarity	NPC149526
0.859	High Similarity	NPC72958
0.859	High Similarity	NPC470675
0.859	High Similarity	NPC133856
0.8589	High Similarity	NPC472622
0.8581	High Similarity	NPC471114
0.8571	High Similarity	NPC125801
0.8571	High Similarity	NPC475106
0.8562	High Similarity	NPC143050
0.8562	High Similarity	NPC117716
0.8562	High Similarity	NPC470674
0.8562	High Similarity	NPC313368
0.8562	High Similarity	NPC470358
0.8562	High Similarity	NPC470673
0.8554	High Similarity	NPC294149
0.8545	High Similarity	NPC472620
0.8544	High Similarity	NPC89625
0.8544	High Similarity	NPC149618
0.8543	High Similarity	NPC469818
0.8537	High Similarity	NPC473202
0.8537	High Similarity	NPC102810
0.8535	High Similarity	NPC154683
0.8535	High Similarity	NPC40356
0.8535	High Similarity	NPC175978
0.8526	High Similarity	NPC474660
0.8516	High Similarity	NPC145467
0.8516	High Similarity	NPC211625
0.8512	High Similarity	NPC473729
0.8512	High Similarity	NPC473607
0.8506	High Similarity	NPC473927
0.8506	High Similarity	NPC163846
0.8506	High Similarity	NPC225173
0.8506	High Similarity	NPC286038
0.8506	High Similarity	NPC237208
0.85	High Similarity	NPC470339
0.8497	Intermediate Similarity	NPC470553
0.8497	Intermediate Similarity	NPC470932
0.8497	Intermediate Similarity	NPC307895
0.8494	Intermediate Similarity	NPC476311
0.8491	Intermediate Similarity	NPC180924
0.8487	Intermediate Similarity	NPC469579
0.8487	Intermediate Similarity	NPC111201
0.8481	Intermediate Similarity	NPC135522
0.8476	Intermediate Similarity	NPC76647
0.8471	Intermediate Similarity	NPC290671
0.8466	Intermediate Similarity	NPC473286
0.8466	Intermediate Similarity	NPC102372
0.8462	Intermediate Similarity	NPC158338
0.8462	Intermediate Similarity	NPC100985
0.8462	Intermediate Similarity	NPC97028
0.8462	Intermediate Similarity	NPC288036
0.8462	Intermediate Similarity	NPC65589
0.8462	Intermediate Similarity	NPC97029
0.8456	Intermediate Similarity	NPC156967
0.8456	Intermediate Similarity	NPC472599
0.8452	Intermediate Similarity	NPC233978
0.8452	Intermediate Similarity	NPC177995
0.8452	Intermediate Similarity	NPC66991
0.8452	Intermediate Similarity	NPC474108
0.8452	Intermediate Similarity	NPC308200
0.8447	Intermediate Similarity	NPC47623
0.8447	Intermediate Similarity	NPC472055
0.8447	Intermediate Similarity	NPC472618
0.8443	Intermediate Similarity	NPC162248
0.8442	Intermediate Similarity	NPC470554
0.8442	Intermediate Similarity	NPC288910
0.8442	Intermediate Similarity	NPC71184
0.8442	Intermediate Similarity	NPC134621
0.8442	Intermediate Similarity	NPC206212
0.8442	Intermediate Similarity	NPC118059
0.8442	Intermediate Similarity	NPC29577
0.8442	Intermediate Similarity	NPC133060
0.8438	Intermediate Similarity	NPC96342
0.8438	Intermediate Similarity	NPC263483
0.8438	Intermediate Similarity	NPC212967
0.8438	Intermediate Similarity	NPC246647
0.8438	Intermediate Similarity	NPC164110
0.8434	Intermediate Similarity	NPC118128
0.8431	Intermediate Similarity	NPC470556
0.8431	Intermediate Similarity	NPC159721
0.8431	Intermediate Similarity	NPC112829
0.8428	Intermediate Similarity	NPC469934
0.8424	Intermediate Similarity	NPC472619
0.8421	Intermediate Similarity	NPC90411
0.8421	Intermediate Similarity	NPC82920
0.8421	Intermediate Similarity	NPC164697
0.8421	Intermediate Similarity	NPC289660
0.8418	Intermediate Similarity	NPC167903
0.8415	Intermediate Similarity	NPC472452
0.8408	Intermediate Similarity	NPC321387
0.8408	Intermediate Similarity	NPC470107
0.8408	Intermediate Similarity	NPC476185
0.8408	Intermediate Similarity	NPC470908
0.8408	Intermediate Similarity	NPC179178
0.8408	Intermediate Similarity	NPC471115
0.8408	Intermediate Similarity	NPC321896
0.8408	Intermediate Similarity	NPC29777
0.8408	Intermediate Similarity	NPC476509
0.8408	Intermediate Similarity	NPC227122
0.8408	Intermediate Similarity	NPC325983
0.8408	Intermediate Similarity	NPC473466
0.8408	Intermediate Similarity	NPC327059
0.8405	Intermediate Similarity	NPC173587
0.8405	Intermediate Similarity	NPC475055
0.8405	Intermediate Similarity	NPC29055
0.8405	Intermediate Similarity	NPC208120
0.84	Intermediate Similarity	NPC245058
0.84	Intermediate Similarity	NPC470983
0.84	Intermediate Similarity	NPC470982
0.8397	Intermediate Similarity	NPC256672
0.8397	Intermediate Similarity	NPC2569
0.8397	Intermediate Similarity	NPC27221
0.8397	Intermediate Similarity	NPC472345
0.8397	Intermediate Similarity	NPC7025
0.8397	Intermediate Similarity	NPC172329
0.8397	Intermediate Similarity	NPC39195
0.8395	Intermediate Similarity	NPC117985
0.8393	Intermediate Similarity	NPC227275
0.8387	Intermediate Similarity	NPC290133
0.8387	Intermediate Similarity	NPC470910
0.8387	Intermediate Similarity	NPC473132
0.8387	Intermediate Similarity	NPC187282
0.8387	Intermediate Similarity	NPC473135
0.8387	Intermediate Similarity	NPC260946
0.8387	Intermediate Similarity	NPC24136
0.8387	Intermediate Similarity	NPC470676
0.8387	Intermediate Similarity	NPC267509
0.8385	Intermediate Similarity	NPC85121
0.8385	Intermediate Similarity	NPC186113
0.8383	Intermediate Similarity	NPC476139
0.8383	Intermediate Similarity	NPC476152
0.8377	Intermediate Similarity	NPC470909
0.8377	Intermediate Similarity	NPC474939
0.8377	Intermediate Similarity	NPC5990
0.8377	Intermediate Similarity	NPC66404
0.8377	Intermediate Similarity	NPC96216
0.8377	Intermediate Similarity	NPC33653
0.8377	Intermediate Similarity	NPC184738

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 NPC477669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	958
0.2-0.3	1823
0.3-0.4	2573
0.4-0.5	1985
0.5-0.6	974
0.6-0.7	374
0.7-0.8	136
0.8-0.85	11
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD2533	Approved
0.906	High Similarity	NPD2532	Approved
0.906	High Similarity	NPD2534	Approved
0.8718	High Similarity	NPD7819	Suspended
0.8457	Intermediate Similarity	NPD5710	Approved
0.8457	Intermediate Similarity	NPD5711	Approved
0.8355	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8105	Intermediate Similarity	NPD2346	Discontinued
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8039	Intermediate Similarity	NPD6100	Approved
0.8039	Intermediate Similarity	NPD6099	Approved
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD7075	Discontinued
0.7988	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6651	Approved
0.7933	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7229	Phase 3
0.7888	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD920	Approved
0.7758	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6559	Discontinued
0.7744	Intermediate Similarity	NPD1934	Approved
0.7711	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2796	Approved
0.7688	Intermediate Similarity	NPD6799	Approved
0.7658	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6801	Discontinued
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD4380	Phase 2
0.761	Intermediate Similarity	NPD3750	Approved
0.761	Intermediate Similarity	NPD4628	Phase 3
0.7605	Intermediate Similarity	NPD3882	Suspended
0.759	Intermediate Similarity	NPD2801	Approved
0.758	Intermediate Similarity	NPD1551	Phase 2
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD37	Approved
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD6273	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1511	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7468	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7074	Phase 3
0.7427	Intermediate Similarity	NPD7199	Phase 2
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7412	Intermediate Similarity	NPD919	Approved
0.7399	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6166	Phase 2
0.7391	Intermediate Similarity	NPD7003	Approved
0.7378	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD1240	Approved
0.7371	Intermediate Similarity	NPD7054	Approved
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7355	Intermediate Similarity	NPD7985	Registered
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5402	Approved
0.733	Intermediate Similarity	NPD7472	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7312	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7288	Intermediate Similarity	NPD5953	Discontinued
0.725	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5405	Approved
0.725	Intermediate Similarity	NPD5404	Approved
0.725	Intermediate Similarity	NPD5406	Approved
0.7247	Intermediate Similarity	NPD7251	Discontinued
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7225	Intermediate Similarity	NPD1247	Approved
0.7216	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7808	Phase 3
0.7197	Intermediate Similarity	NPD8032	Phase 2
0.7191	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6797	Phase 2
0.719	Intermediate Similarity	NPD1283	Approved
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1608	Approved
0.7165	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7783	Phase 2
0.7158	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD2979	Phase 3
0.7151	Intermediate Similarity	NPD7240	Approved
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3764	Approved
0.7126	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4749	Approved
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7117	Intermediate Similarity	NPD6674	Discontinued
0.7114	Intermediate Similarity	NPD7644	Approved
0.7108	Intermediate Similarity	NPD5401	Approved
0.7107	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD230	Phase 1
0.71	Intermediate Similarity	NPD8366	Approved
0.7099	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2344	Approved
0.7099	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6005	Phase 3
0.7099	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD1778	Approved
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7078	Intermediate Similarity	NPD6696	Suspended
0.7073	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4140	Approved
0.7037	Intermediate Similarity	NPD8285	Discontinued
0.7032	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD411	Approved
0.7025	Intermediate Similarity	NPD3268	Approved
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.702	Intermediate Similarity	NPD5691	Approved
0.7006	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD6781	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD6776	Approved
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1471	Phase 3
0.6993	Remote Similarity	NPD1281	Approved
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7698	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6974	Remote Similarity	NPD17	Approved
0.6974	Remote Similarity	NPD4626	Approved
0.6961	Remote Similarity	NPD8491	Approved
0.6948	Remote Similarity	NPD9717	Approved
0.6946	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7870	Phase 2
0.6943	Remote Similarity	NPD7871	Phase 2
0.6939	Remote Similarity	NPD7874	Approved
0.6939	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4307	Phase 2
0.6937	Remote Similarity	NPD4060	Phase 1
0.6936	Remote Similarity	NPD4288	Approved
0.6936	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD2438	Suspended
0.6933	Remote Similarity	NPD7340	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