NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	444.21
Volume:	446.523
LogP:	4.077
LogD:	2.524
LogS:	-3.643
# Rotatable Bonds:	1
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	4.684
Fsp3:	0.68
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:	-4.997
MDCK Permeability:	2.0003828467451967e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	89.0564193725586%
Volume Distribution (VD):	0.875
Pgp-substrate:	8.633753776550293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	8.832
Half-life (T1/2):	0.405

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.279
Carcinogencity:	0.331
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC477675

Natural Product ID:	NPC477675
*Common Name:**	(1S,13R,14R,20S,21R)-21-hydroxy-10-methoxy-1,4,14,19,19-pentamethyl-2,7,18-trioxapentacyclo[11.9.0.03,11.05,9.014,20]docosa-3(11),4,9-triene-8,17-dione
IUPAC Name:	(1S,13R,14R,20S,21R)-21-hydroxy-10-methoxy-1,4,14,19,19-pentamethyl-2,7,18-trioxapentacyclo[11.9.0.03,11.05,9.014,20]docosa-3(11),4,9-triene-8,17-dione
Synonyms:
Standard InCHIKey:	GBKCPBPYMRGRKL-JSGMTKEVSA-N
Standard InCHI:	InChI=1S/C25H32O7/c1-12-14-11-30-22(28)18(14)20(29-6)13-9-16-24(4)8-7-17(27)31-23(2,3)21(24)15(26)10-25(16,5)32-19(12)13/h15-16,21,26H,7-11H2,1-6H3/t15-,16-,21+,24-,25+/m1/s1
SMILES:	CC1=C2COC(=O)C2=C(C3=C1O[C@]4(C[C@H]([C@@H]5[C@@]([C@H]4C3)(CCC(=O)OC5(C)C)C)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118706796
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
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.	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]
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
Others	1

Activity Type	# Activity
Cell Line	1
Others	3

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		Inhibition	=	27.6	%	PMID[24852445]
NPT2	Others	Unspecified		IC50	=	2000	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 NPC477675 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	363
0.1-0.2	1603
0.2-0.3	3372
0.3-0.4	6916
0.4-0.5	11352
0.5-0.6	6158
0.6-0.7	6932
0.7-0.8	5693
0.8-0.85	269
0.85-0.9	26
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC477687
0.9799	High Similarity	NPC477671
0.9733	High Similarity	NPC477674
0.973	High Similarity	NPC477673
0.973	High Similarity	NPC477672
0.9662	High Similarity	NPC477676
0.96	High Similarity	NPC477669
0.9068	High Similarity	NPC477670
0.8889	High Similarity	NPC470359
0.8882	High Similarity	NPC470357
0.8861	High Similarity	NPC239118
0.8861	High Similarity	NPC4950
0.8824	High Similarity	NPC8817
0.8765	High Similarity	NPC125465
0.8758	High Similarity	NPC100849
0.8742	High Similarity	NPC218818
0.8726	High Similarity	NPC472799
0.8693	High Similarity	NPC75694
0.8679	High Similarity	NPC158542
0.865	High Similarity	NPC472621
0.8625	High Similarity	NPC472617
0.8616	High Similarity	NPC4547
0.8599	High Similarity	NPC470675
0.8599	High Similarity	NPC473131
0.8598	High Similarity	NPC472622
0.8589	High Similarity	NPC314653
0.8589	High Similarity	NPC316262
0.8581	High Similarity	NPC137296
0.8581	High Similarity	NPC245757
0.8581	High Similarity	NPC304351
0.858	High Similarity	NPC473022
0.8563	High Similarity	NPC294149
0.8554	High Similarity	NPC472620
0.8544	High Similarity	NPC217447
0.8544	High Similarity	NPC271681
0.8544	High Similarity	NPC273483
0.8535	High Similarity	NPC150928
0.8526	High Similarity	NPC472345
0.8512	High Similarity	NPC324220
0.8512	High Similarity	NPC472661
0.8512	High Similarity	NPC312630
0.8494	Intermediate Similarity	NPC313717
0.8494	Intermediate Similarity	NPC315306
0.8494	Intermediate Similarity	NPC477571
0.8494	Intermediate Similarity	NPC477572
0.8494	Intermediate Similarity	NPC477573
0.8476	Intermediate Similarity	NPC102372
0.8476	Intermediate Similarity	NPC146584
0.8476	Intermediate Similarity	NPC21016
0.8467	Intermediate Similarity	NPC472599
0.8467	Intermediate Similarity	NPC156967
0.8462	Intermediate Similarity	NPC474108
0.8462	Intermediate Similarity	NPC177995
0.8457	Intermediate Similarity	NPC470810
0.8457	Intermediate Similarity	NPC472618
0.8457	Intermediate Similarity	NPC470358
0.8447	Intermediate Similarity	NPC196448
0.8447	Intermediate Similarity	NPC272196
0.8442	Intermediate Similarity	NPC472344
0.8434	Intermediate Similarity	NPC472619
0.8434	Intermediate Similarity	NPC213416
0.8434	Intermediate Similarity	NPC102810
0.8434	Intermediate Similarity	NPC473202
0.8431	Intermediate Similarity	NPC469818
0.8428	Intermediate Similarity	NPC87708
0.8421	Intermediate Similarity	NPC475656
0.8421	Intermediate Similarity	NPC475148
0.8418	Intermediate Similarity	NPC119929
0.8418	Intermediate Similarity	NPC179178
0.8418	Intermediate Similarity	NPC202595
0.8415	Intermediate Similarity	NPC208120
0.8415	Intermediate Similarity	NPC173587
0.8412	Intermediate Similarity	NPC473607
0.8412	Intermediate Similarity	NPC473729
0.8411	Intermediate Similarity	NPC245058
0.8405	Intermediate Similarity	NPC117985
0.8397	Intermediate Similarity	NPC286038
0.8395	Intermediate Similarity	NPC470339
0.8395	Intermediate Similarity	NPC474373
0.8393	Intermediate Similarity	NPC476311
0.8385	Intermediate Similarity	NPC146211
0.8383	Intermediate Similarity	NPC17219
0.8377	Intermediate Similarity	NPC469579
0.8373	Intermediate Similarity	NPC232936
0.8365	Intermediate Similarity	NPC72958
0.8365	Intermediate Similarity	NPC478148
0.8365	Intermediate Similarity	NPC232645
0.8354	Intermediate Similarity	NPC291049
0.8354	Intermediate Similarity	NPC233267
0.8344	Intermediate Similarity	NPC313368
0.8344	Intermediate Similarity	NPC66991
0.8344	Intermediate Similarity	NPC472055
0.8333	Intermediate Similarity	NPC288910
0.8333	Intermediate Similarity	NPC133060
0.8333	Intermediate Similarity	NPC118059
0.8333	Intermediate Similarity	NPC470554
0.8333	Intermediate Similarity	NPC470674
0.8333	Intermediate Similarity	NPC470673
0.8333	Intermediate Similarity	NPC117716
0.8313	Intermediate Similarity	NPC473770
0.8313	Intermediate Similarity	NPC475131
0.8313	Intermediate Similarity	NPC167903
0.8313	Intermediate Similarity	NPC473509
0.8313	Intermediate Similarity	NPC472452
0.8303	Intermediate Similarity	NPC29055
0.8303	Intermediate Similarity	NPC475055
0.8303	Intermediate Similarity	NPC478044
0.8302	Intermediate Similarity	NPC158866
0.8302	Intermediate Similarity	NPC470908
0.8291	Intermediate Similarity	NPC211625
0.8291	Intermediate Similarity	NPC37139
0.8291	Intermediate Similarity	NPC105415
0.8289	Intermediate Similarity	NPC470983
0.8289	Intermediate Similarity	NPC470982
0.8282	Intermediate Similarity	NPC186113
0.8282	Intermediate Similarity	NPC472299
0.8282	Intermediate Similarity	NPC478042
0.828	Intermediate Similarity	NPC470910
0.8272	Intermediate Similarity	NPC164427
0.8269	Intermediate Similarity	NPC112749
0.8269	Intermediate Similarity	NPC470909
0.8269	Intermediate Similarity	NPC33653
0.8269	Intermediate Similarity	NPC184738
0.8269	Intermediate Similarity	NPC470553
0.8269	Intermediate Similarity	NPC474939
0.8269	Intermediate Similarity	NPC470932
0.8269	Intermediate Similarity	NPC307895
0.8269	Intermediate Similarity	NPC96216
0.8266	Intermediate Similarity	NPC472663
0.8266	Intermediate Similarity	NPC472662
0.8263	Intermediate Similarity	NPC225419
0.8261	Intermediate Similarity	NPC210942
0.8261	Intermediate Similarity	NPC169990
0.8261	Intermediate Similarity	NPC135522
0.8258	Intermediate Similarity	NPC285659
0.8258	Intermediate Similarity	NPC157497
0.8258	Intermediate Similarity	NPC81337
0.8258	Intermediate Similarity	NPC111201
0.8253	Intermediate Similarity	NPC473286
0.8253	Intermediate Similarity	NPC112981
0.825	Intermediate Similarity	NPC149526
0.825	Intermediate Similarity	NPC474417
0.825	Intermediate Similarity	NPC133856
0.825	Intermediate Similarity	NPC290671
0.825	Intermediate Similarity	NPC48671
0.8246	Intermediate Similarity	NPC476199
0.8246	Intermediate Similarity	NPC233978
0.8246	Intermediate Similarity	NPC476210
0.8242	Intermediate Similarity	NPC475106
0.8242	Intermediate Similarity	NPC473961
0.8242	Intermediate Similarity	NPC472402
0.8239	Intermediate Similarity	NPC471114
0.8239	Intermediate Similarity	NPC270160
0.8239	Intermediate Similarity	NPC237440
0.8235	Intermediate Similarity	NPC162248
0.8235	Intermediate Similarity	NPC289147
0.8232	Intermediate Similarity	NPC143050
0.8228	Intermediate Similarity	NPC285748
0.8228	Intermediate Similarity	NPC125801
0.8225	Intermediate Similarity	NPC118128
0.8221	Intermediate Similarity	NPC282390
0.8221	Intermediate Similarity	NPC123153
0.8221	Intermediate Similarity	NPC281137
0.8217	Intermediate Similarity	NPC206212
0.8217	Intermediate Similarity	NPC71184
0.8214	Intermediate Similarity	NPC191653
0.821	Intermediate Similarity	NPC175192
0.821	Intermediate Similarity	NPC89625
0.821	Intermediate Similarity	NPC149618
0.8205	Intermediate Similarity	NPC159721
0.8205	Intermediate Similarity	NPC294432
0.8205	Intermediate Similarity	NPC469542
0.8205	Intermediate Similarity	NPC470556
0.8205	Intermediate Similarity	NPC471731
0.8205	Intermediate Similarity	NPC112829
0.8205	Intermediate Similarity	NPC51106
0.8204	Intermediate Similarity	NPC20216
0.8199	Intermediate Similarity	NPC113608
0.8199	Intermediate Similarity	NPC470340
0.8199	Intermediate Similarity	NPC40356
0.8199	Intermediate Similarity	NPC175978
0.8199	Intermediate Similarity	NPC114880
0.8199	Intermediate Similarity	NPC268992
0.8199	Intermediate Similarity	NPC51824
0.8199	Intermediate Similarity	NPC474843
0.8199	Intermediate Similarity	NPC154683
0.8199	Intermediate Similarity	NPC470338
0.8199	Intermediate Similarity	NPC470337
0.8194	Intermediate Similarity	NPC472605
0.8194	Intermediate Similarity	NPC164697
0.8194	Intermediate Similarity	NPC472604
0.8194	Intermediate Similarity	NPC289660
0.8194	Intermediate Similarity	NPC82920
0.8193	Intermediate Similarity	NPC156082
0.8187	Intermediate Similarity	NPC227275
0.8187	Intermediate Similarity	NPC475233
0.8187	Intermediate Similarity	NPC476509
0.8187	Intermediate Similarity	NPC474660
0.8187	Intermediate Similarity	NPC478050
0.8187	Intermediate Similarity	NPC321387

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 NPC477675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	1069
0.2-0.3	2071
0.3-0.4	2553
0.4-0.5	1932
0.5-0.6	800
0.6-0.7	319
0.7-0.8	80
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8693	High Similarity	NPD2533	Approved
0.8693	High Similarity	NPD2532	Approved
0.8693	High Similarity	NPD2534	Approved
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD5710	Approved
0.8133	Intermediate Similarity	NPD5711	Approved
0.8129	Intermediate Similarity	NPD2800	Approved
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.7947	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD6651	Approved
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7798	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6599	Discontinued
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7679	Intermediate Similarity	NPD3749	Approved
0.7657	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6801	Discontinued
0.7602	Intermediate Similarity	NPD7229	Phase 3
0.7576	Intermediate Similarity	NPD3226	Approved
0.7561	Intermediate Similarity	NPD920	Approved
0.7547	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1934	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.753	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7484	Intermediate Similarity	NPD2796	Approved
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3817	Phase 2
0.7452	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5124	Phase 1
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3818	Discontinued
0.7427	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD5760	Phase 2
0.7396	Intermediate Similarity	NPD5761	Phase 2
0.7394	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6799	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD7985	Registered
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1243	Approved
0.7345	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6166	Phase 2
0.7314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3882	Suspended
0.7301	Intermediate Similarity	NPD3750	Approved
0.7294	Intermediate Similarity	NPD1465	Phase 2
0.7294	Intermediate Similarity	NPD2801	Approved
0.7288	Intermediate Similarity	NPD7054	Approved
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5402	Approved
0.7247	Intermediate Similarity	NPD7472	Approved
0.7241	Intermediate Similarity	NPD7199	Phase 2
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7228	Approved
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3748	Approved
0.7205	Intermediate Similarity	NPD1510	Phase 2
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7286	Phase 2
0.7188	Intermediate Similarity	NPD1607	Approved
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1511	Approved
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7127	Intermediate Similarity	NPD7808	Phase 3
0.7127	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD919	Approved
0.7111	Intermediate Similarity	NPD6797	Phase 2
0.7104	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7091	Intermediate Similarity	NPD7003	Approved
0.7091	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7072	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD1240	Approved
0.7062	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7041	Intermediate Similarity	NPD5403	Approved
0.7039	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8366	Approved
0.703	Intermediate Similarity	NPD6674	Discontinued
0.7024	Intermediate Similarity	NPD5401	Approved
0.702	Intermediate Similarity	NPD7644	Approved
0.7017	Intermediate Similarity	NPD5953	Discontinued
0.7012	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6004	Phase 3
0.7012	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6005	Phase 3
0.7012	Intermediate Similarity	NPD6002	Phase 3
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4625	Phase 3
0.6957	Remote Similarity	NPD4140	Approved
0.6951	Remote Similarity	NPD5405	Approved
0.6951	Remote Similarity	NPD5408	Approved
0.6951	Remote Similarity	NPD5404	Approved
0.6951	Remote Similarity	NPD5406	Approved
0.6949	Remote Similarity	NPD1247	Approved
0.6944	Remote Similarity	NPD3751	Discontinued
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6918	Remote Similarity	NPD6832	Phase 2
0.6907	Remote Similarity	NPD7697	Approved
0.6907	Remote Similarity	NPD7696	Phase 3
0.6907	Remote Similarity	NPD7698	Approved
0.6899	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4287	Approved
0.6894	Remote Similarity	NPD8032	Phase 2
0.6893	Remote Similarity	NPD8491	Approved
0.6879	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD6696	Suspended
0.6875	Remote Similarity	NPD8285	Discontinued
0.6872	Remote Similarity	NPD3926	Phase 2
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD7870	Phase 2
0.6869	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7874	Approved
0.6859	Remote Similarity	NPD1608	Approved
0.6852	Remote Similarity	NPD2979	Phase 3
0.6851	Remote Similarity	NPD7177	Discontinued
0.6848	Remote Similarity	NPD4477	Approved
0.6848	Remote Similarity	NPD4476	Approved
0.6842	Remote Similarity	NPD4363	Phase 3
0.6842	Remote Similarity	NPD7340	Approved
0.6842	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4360	Phase 2
0.6833	Remote Similarity	NPD2403	Approved
0.6832	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3764	Approved
0.6826	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4749	Approved
0.681	Remote Similarity	NPD230	Phase 1
0.681	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6355	Discontinued
0.6807	Remote Similarity	NPD2344	Approved
0.6807	Remote Similarity	NPD5763	Approved
0.6807	Remote Similarity	NPD5762	Approved
0.6805	Remote Similarity	NPD7236	Approved
0.68	Remote Similarity	NPD8455	Phase 2
0.6793	Remote Similarity	NPD6764	Approved
0.6793	Remote Similarity	NPD6765	Approved
0.6788	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD8320	Phase 1
0.6786	Remote Similarity	NPD8319	Approved
0.6779	Remote Similarity	NPD8469	Approved
0.6774	Remote Similarity	NPD1778	Approved
0.6769	Remote Similarity	NPD6823	Phase 2
0.6768	Remote Similarity	NPD7701	Phase 2
0.6761	Remote Similarity	NPD5353	Approved
0.6754	Remote Similarity	NPD6534	Approved
0.6754	Remote Similarity	NPD6535	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