NPASS Compound

Structure

NPC475717 OpenBabel07101718192D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.2956 0.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0101 1.6613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4029 -3.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4915 -1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6873 0.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9387 -1.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9387 0.0529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4915 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4029 -0.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0101 -1.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6873 -1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8831 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0101 0.0529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8831 -1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0815 -3.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5458 -0.7512 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3315 -0.7512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6873 -2.6084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2869 -2.3856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8471 -3.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5458 0.8571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5458 -3.9679 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 8 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 9 1 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 9 18 2 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	2.602
LogD:	1.238
LogS:	-3.97
# Rotatable Bonds:	3
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.814
Synthetic Accessibility Score:	4.144
Fsp3:	0.235
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:	-4.92
MDCK Permeability:	2.403072539891582e-05
Pgp-inhibitor:	0.094
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.129
20% Bioavailability (F20%):	0.783
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	89.42304229736328%
Volume Distribution (VD):	0.562
Pgp-substrate:	6.172662258148193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.721
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.433
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	6.065
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.717
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.667
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.806
Skin Sensitization:	0.762
Carcinogencity:	0.796
Eye Corrosion:	0.004
Eye Irritation:	0.05
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC475717

Natural Product ID:	NPC475717
*Common Name:**	Geodin
IUPAC Name:	methyl 4-hydroxy-5'-methoxy-6-methyl-3,3'-dioxospiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate
Synonyms:	Geodin
Standard InCHIKey:	JCMPRFCVZKOFIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-8-4-11(19)14-12(5-8)24-17(15(14)20)10(16(21)23-3)6-9(18)7-13(17)22-2/h4-7,19H,1-3H3
SMILES:	CC1=CC(=C2C(=C1)OC3(C2=O)C(=CC(=O)C=C3OC)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512514
PubChem CID:	168966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO32471	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809055]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	LD90	=	50.0	ppm	PMID[573957]

☑ 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 NPC475717 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	351
0.1-0.2	1555
0.2-0.3	4009
0.3-0.4	8852
0.4-0.5	9567
0.5-0.6	3919
0.6-0.7	6128
0.7-0.8	7249
0.8-0.85	1016
0.85-0.9	44
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC237560
0.9139	High Similarity	NPC301233
0.902	High Similarity	NPC154341
0.8994	High Similarity	NPC72696
0.8947	High Similarity	NPC275878
0.8933	High Similarity	NPC228012
0.8839	High Similarity	NPC476930
0.8836	High Similarity	NPC268691
0.8831	High Similarity	NPC326910
0.8774	High Similarity	NPC272550
0.8758	High Similarity	NPC39819
0.8733	High Similarity	NPC316535
0.8726	High Similarity	NPC130955
0.8726	High Similarity	NPC313368
0.8671	High Similarity	NPC476929
0.8671	High Similarity	NPC117985
0.8645	High Similarity	NPC198236
0.8627	High Similarity	NPC70764
0.8627	High Similarity	NPC285527
0.8627	High Similarity	NPC106334
0.8608	High Similarity	NPC284918
0.8608	High Similarity	NPC243701
0.86	High Similarity	NPC476310
0.86	High Similarity	NPC476164
0.8581	High Similarity	NPC253904
0.8581	High Similarity	NPC321363
0.8581	High Similarity	NPC271681
0.8581	High Similarity	NPC281272
0.8571	High Similarity	NPC116822
0.8571	High Similarity	NPC213382
0.8571	High Similarity	NPC164527
0.8562	High Similarity	NPC211811
0.8562	High Similarity	NPC172329
0.8562	High Similarity	NPC476931
0.8562	High Similarity	NPC2569
0.8543	High Similarity	NPC105381
0.8543	High Similarity	NPC10302
0.8535	High Similarity	NPC313922
0.8535	High Similarity	NPC472050
0.8528	High Similarity	NPC313717
0.8528	High Similarity	NPC315306
0.8523	High Similarity	NPC230902
0.8514	High Similarity	NPC98395
0.8509	High Similarity	NPC314653
0.8509	High Similarity	NPC316262
0.8506	High Similarity	NPC477941
0.8506	High Similarity	NPC198927
0.8497	Intermediate Similarity	NPC17816
0.8491	Intermediate Similarity	NPC43490
0.8491	Intermediate Similarity	NPC475107
0.8487	Intermediate Similarity	NPC71210
0.8487	Intermediate Similarity	NPC98926
0.8487	Intermediate Similarity	NPC469764
0.8487	Intermediate Similarity	NPC28632
0.8481	Intermediate Similarity	NPC246466
0.8467	Intermediate Similarity	NPC145673
0.8462	Intermediate Similarity	NPC304954
0.8457	Intermediate Similarity	NPC62444
0.8457	Intermediate Similarity	NPC323137
0.8452	Intermediate Similarity	NPC180351
0.8452	Intermediate Similarity	NPC267117
0.8452	Intermediate Similarity	NPC167576
0.8452	Intermediate Similarity	NPC470107
0.8452	Intermediate Similarity	NPC295036
0.8442	Intermediate Similarity	NPC191634
0.8431	Intermediate Similarity	NPC196114
0.8431	Intermediate Similarity	NPC469758
0.8428	Intermediate Similarity	NPC195832
0.8421	Intermediate Similarity	NPC470216
0.8408	Intermediate Similarity	NPC72370
0.8408	Intermediate Similarity	NPC470331
0.8405	Intermediate Similarity	NPC95715
0.8397	Intermediate Similarity	NPC295650
0.8397	Intermediate Similarity	NPC471229
0.8395	Intermediate Similarity	NPC88243
0.8389	Intermediate Similarity	NPC287068
0.8387	Intermediate Similarity	NPC4423
0.8387	Intermediate Similarity	NPC277032
0.8387	Intermediate Similarity	NPC77325
0.8387	Intermediate Similarity	NPC73236
0.8385	Intermediate Similarity	NPC94796
0.8385	Intermediate Similarity	NPC475106
0.8385	Intermediate Similarity	NPC272722
0.8383	Intermediate Similarity	NPC477682
0.8383	Intermediate Similarity	NPC477683
0.8377	Intermediate Similarity	NPC129650
0.8377	Intermediate Similarity	NPC46941
0.8377	Intermediate Similarity	NPC146884
0.8375	Intermediate Similarity	NPC471744
0.8375	Intermediate Similarity	NPC269906
0.8375	Intermediate Similarity	NPC470810
0.8366	Intermediate Similarity	NPC474309
0.8366	Intermediate Similarity	NPC475923
0.8365	Intermediate Similarity	NPC473395
0.8355	Intermediate Similarity	NPC1534
0.8355	Intermediate Similarity	NPC471520
0.8354	Intermediate Similarity	NPC473096
0.8354	Intermediate Similarity	NPC471456
0.8354	Intermediate Similarity	NPC317585
0.8354	Intermediate Similarity	NPC478221
0.8354	Intermediate Similarity	NPC473095
0.8344	Intermediate Similarity	NPC476255
0.8344	Intermediate Similarity	NPC29160
0.8344	Intermediate Similarity	NPC256141
0.8344	Intermediate Similarity	NPC75069
0.8344	Intermediate Similarity	NPC90411
0.8343	Intermediate Similarity	NPC475656
0.8343	Intermediate Similarity	NPC475148
0.8333	Intermediate Similarity	NPC260582
0.8333	Intermediate Similarity	NPC119929
0.8333	Intermediate Similarity	NPC18457
0.8333	Intermediate Similarity	NPC477677
0.8333	Intermediate Similarity	NPC472582
0.8333	Intermediate Similarity	NPC34910
0.8333	Intermediate Similarity	NPC225129
0.8333	Intermediate Similarity	NPC150928
0.8333	Intermediate Similarity	NPC25427
0.8333	Intermediate Similarity	NPC112757
0.8333	Intermediate Similarity	NPC472421
0.8333	Intermediate Similarity	NPC158866
0.8333	Intermediate Similarity	NPC264756
0.8323	Intermediate Similarity	NPC112418
0.8323	Intermediate Similarity	NPC37139
0.8323	Intermediate Similarity	NPC19545
0.8313	Intermediate Similarity	NPC55738
0.8313	Intermediate Similarity	NPC154986
0.8313	Intermediate Similarity	NPC125969
0.8312	Intermediate Similarity	NPC260946
0.8312	Intermediate Similarity	NPC130176
0.8312	Intermediate Similarity	NPC99454
0.8312	Intermediate Similarity	NPC209278
0.8312	Intermediate Similarity	NPC229190
0.8303	Intermediate Similarity	NPC476641
0.8303	Intermediate Similarity	NPC28042
0.8302	Intermediate Similarity	NPC474638
0.8302	Intermediate Similarity	NPC265511
0.8302	Intermediate Similarity	NPC180924
0.8302	Intermediate Similarity	NPC45131
0.8301	Intermediate Similarity	NPC473812
0.8301	Intermediate Similarity	NPC473813
0.8301	Intermediate Similarity	NPC274085
0.8301	Intermediate Similarity	NPC89664
0.8293	Intermediate Similarity	NPC193222
0.8293	Intermediate Similarity	NPC473094
0.8293	Intermediate Similarity	NPC234331
0.8291	Intermediate Similarity	NPC141212
0.8291	Intermediate Similarity	NPC203080
0.8291	Intermediate Similarity	NPC478231
0.8291	Intermediate Similarity	NPC189130
0.8291	Intermediate Similarity	NPC472799
0.8289	Intermediate Similarity	NPC136840
0.8289	Intermediate Similarity	NPC310128
0.8289	Intermediate Similarity	NPC171870
0.8288	Intermediate Similarity	NPC324488
0.8282	Intermediate Similarity	NPC189689
0.8282	Intermediate Similarity	NPC204088
0.8282	Intermediate Similarity	NPC259007
0.8282	Intermediate Similarity	NPC36320
0.8282	Intermediate Similarity	NPC329215
0.8282	Intermediate Similarity	NPC473908
0.828	Intermediate Similarity	NPC115324
0.828	Intermediate Similarity	NPC474744
0.828	Intermediate Similarity	NPC240768
0.828	Intermediate Similarity	NPC106372
0.828	Intermediate Similarity	NPC475076
0.828	Intermediate Similarity	NPC470380
0.828	Intermediate Similarity	NPC236769
0.828	Intermediate Similarity	NPC76376
0.828	Intermediate Similarity	NPC472423
0.828	Intermediate Similarity	NPC260895
0.828	Intermediate Similarity	NPC200773
0.828	Intermediate Similarity	NPC474772
0.828	Intermediate Similarity	NPC170169
0.828	Intermediate Similarity	NPC58668
0.8278	Intermediate Similarity	NPC49242
0.8274	Intermediate Similarity	NPC98546
0.8272	Intermediate Similarity	NPC471745
0.8269	Intermediate Similarity	NPC200221
0.8269	Intermediate Similarity	NPC84142
0.8269	Intermediate Similarity	NPC294502
0.8269	Intermediate Similarity	NPC269420
0.8269	Intermediate Similarity	NPC291049
0.8269	Intermediate Similarity	NPC159103
0.8269	Intermediate Similarity	NPC178202
0.8269	Intermediate Similarity	NPC233267
0.8269	Intermediate Similarity	NPC474052
0.8267	Intermediate Similarity	NPC254841
0.8267	Intermediate Similarity	NPC221046
0.8267	Intermediate Similarity	NPC332594
0.8261	Intermediate Similarity	NPC304839
0.8261	Intermediate Similarity	NPC220582
0.8258	Intermediate Similarity	NPC117463
0.8258	Intermediate Similarity	NPC472918
0.8258	Intermediate Similarity	NPC86847
0.8258	Intermediate Similarity	NPC259632
0.8258	Intermediate Similarity	NPC469425
0.8258	Intermediate Similarity	NPC21835
0.8258	Intermediate Similarity	NPC202494
0.8258	Intermediate Similarity	NPC71055
0.8258	Intermediate Similarity	NPC137296

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 NPC475717 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	944
0.2-0.3	1873
0.3-0.4	2539
0.4-0.5	1892
0.5-0.6	1049
0.6-0.7	375
0.7-0.8	153
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8418	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD1551	Phase 2
0.8301	Intermediate Similarity	NPD6799	Approved
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD2534	Approved
0.8247	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD5401	Approved
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD447	Suspended
0.8039	Intermediate Similarity	NPD2800	Approved
0.8038	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD1934	Approved
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD919	Approved
0.7962	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD2801	Approved
0.7939	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7904	Intermediate Similarity	NPD7473	Discontinued
0.7867	Intermediate Similarity	NPD1240	Approved
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD411	Approved
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.784	Intermediate Similarity	NPD7819	Suspended
0.784	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1511	Approved
0.7806	Intermediate Similarity	NPD1243	Approved
0.7799	Intermediate Similarity	NPD920	Approved
0.7793	Intermediate Similarity	NPD9717	Approved
0.7792	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD1247	Approved
0.7755	Intermediate Similarity	NPD1203	Approved
0.7738	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6166	Phase 2
0.7733	Intermediate Similarity	NPD2313	Discontinued
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7411	Suspended
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7673	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3748	Approved
0.7662	Intermediate Similarity	NPD4308	Phase 3
0.7654	Intermediate Similarity	NPD4380	Phase 2
0.7636	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD5710	Approved
0.7619	Intermediate Similarity	NPD5711	Approved
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7613	Intermediate Similarity	NPD2796	Approved
0.7605	Intermediate Similarity	NPD5494	Approved
0.7602	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD230	Phase 1
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.7564	Intermediate Similarity	NPD2344	Approved
0.756	Intermediate Similarity	NPD6959	Discontinued
0.7557	Intermediate Similarity	NPD8434	Phase 2
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD2403	Approved
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7457	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD9493	Approved
0.7427	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5953	Discontinued
0.7403	Intermediate Similarity	NPD4307	Phase 2
0.7399	Intermediate Similarity	NPD7054	Approved
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2309	Approved
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7472	Approved
0.7355	Intermediate Similarity	NPD1933	Approved
0.7351	Intermediate Similarity	NPD1019	Discontinued
0.7342	Intermediate Similarity	NPD1471	Phase 3
0.7337	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6651	Approved
0.7299	Intermediate Similarity	NPD7286	Phase 2
0.729	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD37	Approved
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD4965	Approved
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7215	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1608	Approved
0.7171	Intermediate Similarity	NPD1470	Approved
0.7171	Intermediate Similarity	NPD2797	Approved
0.7169	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD2354	Approved
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2798	Approved
0.7114	Intermediate Similarity	NPD1778	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7091	Intermediate Similarity	NPD5049	Phase 3
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD4288	Approved
0.7055	Intermediate Similarity	NPD6190	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7047	Intermediate Similarity	NPD7874	Approved
0.7047	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2654	Approved
0.7032	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5762	Approved
0.7019	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2353	Approved
0.7019	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6004	Phase 3
0.7019	Intermediate Similarity	NPD6005	Phase 3
0.7019	Intermediate Similarity	NPD6002	Phase 3
0.7019	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.6995	Remote Similarity	NPD4287	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6987	Remote Similarity	NPD7095	Approved
0.698	Remote Similarity	NPD9545	Approved
0.6974	Remote Similarity	NPD9269	Phase 2
0.697	Remote Similarity	NPD7390	Discontinued
0.6963	Remote Similarity	NPD7870	Phase 2
0.6963	Remote Similarity	NPD7871	Phase 2
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5405	Approved
0.6957	Remote Similarity	NPD5408	Approved
0.6957	Remote Similarity	NPD5404	Approved
0.6957	Remote Similarity	NPD5406	Approved
0.6954	Remote Similarity	NPD3496	Discontinued
0.6954	Remote Similarity	NPD7199	Phase 2
0.6951	Remote Similarity	NPD3887	Approved
0.6949	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7228	Approved
0.6948	Remote Similarity	NPD3267	Approved
0.6948	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD690	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