NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	281.005
LogP:	1.229
LogD:	1.164
LogS:	-2.805
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	5.506
Fsp3:	0.8
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:	-4.503
MDCK Permeability:	3.3538060961291194e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.884
30% Bioavailability (F30%):	0.77

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.699
Plasma Protein Binding (PPB):	32.90068435668945%
Volume Distribution (VD):	1.438
Pgp-substrate:	61.39511489868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	9.187
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.262
Carcinogencity:	0.967
Eye Corrosion:	0.021
Eye Irritation:	0.178
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC227494

Natural Product ID:	NPC227494
*Common Name:**	Pestafolide A
IUPAC Name:	(3S,6S,6'S,7R)-6,7-dihydroxy-6',7-dimethylspiro[1,4,5,6-tetrahydroisochromene-3,2'-oxane]-8-one
Synonyms:	Pestafolide A
Standard InCHIKey:	BKSQJYOLLWNPIP-GGZSPTBLSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-9-4-3-5-15(20-9)7-10-6-12(16)14(2,18)13(17)11(10)8-19-15/h9,12,16,18H,3-8H2,1-2H3/t9-,12-,14+,15-/m0/s1
SMILES:	C[C@H]1CCC[C@@]2(O1)OCC1=C(C2)C[C@@H]([C@@](C1=O)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465048
PubChem CID:	24850054
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO32872	pestalotiopsis foedan	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288805]

☑ 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
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IZ	=	10.0	mm	PMID[555932]

☑ 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 NPC227494 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	217
0.1-0.2	1464
0.2-0.3	4892
0.3-0.4	8709
0.4-0.5	15584
0.5-0.6	8198
0.6-0.7	3429
0.7-0.8	201
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.798	Intermediate Similarity	NPC266842
0.7664	Intermediate Similarity	NPC89408
0.76	Intermediate Similarity	NPC473334
0.7596	Intermediate Similarity	NPC320154
0.7589	Intermediate Similarity	NPC232258
0.7547	Intermediate Similarity	NPC469853
0.7525	Intermediate Similarity	NPC143446
0.75	Intermediate Similarity	NPC39996
0.75	Intermediate Similarity	NPC471496
0.7477	Intermediate Similarity	NPC151393
0.7456	Intermediate Similarity	NPC129434
0.7431	Intermediate Similarity	NPC317107
0.7429	Intermediate Similarity	NPC159533
0.7414	Intermediate Similarity	NPC470922
0.7404	Intermediate Similarity	NPC207885
0.7396	Intermediate Similarity	NPC473353
0.7383	Intermediate Similarity	NPC266514
0.7364	Intermediate Similarity	NPC317687
0.7353	Intermediate Similarity	NPC94337
0.7345	Intermediate Similarity	NPC291564
0.7315	Intermediate Similarity	NPC322903
0.7304	Intermediate Similarity	NPC476204
0.7304	Intermediate Similarity	NPC170084
0.73	Intermediate Similarity	NPC472010
0.73	Intermediate Similarity	NPC73457
0.7282	Intermediate Similarity	NPC20066
0.7282	Intermediate Similarity	NPC471916
0.7282	Intermediate Similarity	NPC471694
0.7281	Intermediate Similarity	NPC475775
0.7281	Intermediate Similarity	NPC476529
0.7273	Intermediate Similarity	NPC146945
0.7273	Intermediate Similarity	NPC171888
0.7264	Intermediate Similarity	NPC291154
0.7264	Intermediate Similarity	NPC99266
0.7264	Intermediate Similarity	NPC309398
0.7264	Intermediate Similarity	NPC131366
0.7264	Intermediate Similarity	NPC151516
0.7257	Intermediate Similarity	NPC477116
0.7257	Intermediate Similarity	NPC27999
0.7248	Intermediate Similarity	NPC31522
0.7248	Intermediate Similarity	NPC87335
0.7248	Intermediate Similarity	NPC101018
0.7238	Intermediate Similarity	NPC305085
0.7238	Intermediate Similarity	NPC112613
0.7238	Intermediate Similarity	NPC84042
0.7228	Intermediate Similarity	NPC471483
0.7228	Intermediate Similarity	NPC271652
0.7217	Intermediate Similarity	NPC107338
0.7217	Intermediate Similarity	NPC109607
0.7217	Intermediate Similarity	NPC112038
0.7216	Intermediate Similarity	NPC187529
0.7212	Intermediate Similarity	NPC306908
0.7212	Intermediate Similarity	NPC212465
0.7212	Intermediate Similarity	NPC177232
0.72	Intermediate Similarity	NPC113393
0.7196	Intermediate Similarity	NPC296950
0.7193	Intermediate Similarity	NPC251310
0.7193	Intermediate Similarity	NPC204552
0.7193	Intermediate Similarity	NPC188667
0.7193	Intermediate Similarity	NPC297179
0.7184	Intermediate Similarity	NPC473291
0.7182	Intermediate Similarity	NPC235014
0.7172	Intermediate Similarity	NPC106051
0.7172	Intermediate Similarity	NPC307298
0.717	Intermediate Similarity	NPC469606
0.717	Intermediate Similarity	NPC273005
0.717	Intermediate Similarity	NPC295791
0.717	Intermediate Similarity	NPC313569
0.717	Intermediate Similarity	NPC80781
0.717	Intermediate Similarity	NPC31058
0.717	Intermediate Similarity	NPC201191
0.717	Intermediate Similarity	NPC137430
0.717	Intermediate Similarity	NPC223834
0.7167	Intermediate Similarity	NPC476966
0.7157	Intermediate Similarity	NPC2003
0.7157	Intermediate Similarity	NPC25701
0.7156	Intermediate Similarity	NPC469916
0.7156	Intermediate Similarity	NPC473807
0.7156	Intermediate Similarity	NPC300614
0.7156	Intermediate Similarity	NPC472439
0.7156	Intermediate Similarity	NPC90946
0.7143	Intermediate Similarity	NPC472972
0.7143	Intermediate Similarity	NPC472644
0.7143	Intermediate Similarity	NPC159333
0.7143	Intermediate Similarity	NPC51978
0.7143	Intermediate Similarity	NPC208998
0.7143	Intermediate Similarity	NPC311592
0.7143	Intermediate Similarity	NPC75167
0.7143	Intermediate Similarity	NPC7921
0.713	Intermediate Similarity	NPC476740
0.713	Intermediate Similarity	NPC268958
0.713	Intermediate Similarity	NPC476738
0.7119	Intermediate Similarity	NPC318135
0.7119	Intermediate Similarity	NPC24651
0.7117	Intermediate Similarity	NPC201992
0.7117	Intermediate Similarity	NPC324683
0.7115	Intermediate Similarity	NPC20078
0.7115	Intermediate Similarity	NPC218064
0.7115	Intermediate Similarity	NPC473574
0.7113	Intermediate Similarity	NPC60951
0.7107	Intermediate Similarity	NPC173347
0.7105	Intermediate Similarity	NPC474483
0.7103	Intermediate Similarity	NPC474581
0.7103	Intermediate Similarity	NPC8196
0.7103	Intermediate Similarity	NPC473816
0.7103	Intermediate Similarity	NPC104161
0.7103	Intermediate Similarity	NPC118902
0.7103	Intermediate Similarity	NPC472747
0.7103	Intermediate Similarity	NPC475367
0.7103	Intermediate Similarity	NPC472750
0.7103	Intermediate Similarity	NPC471208
0.7103	Intermediate Similarity	NPC469980
0.71	Intermediate Similarity	NPC471054
0.7094	Intermediate Similarity	NPC312833
0.7091	Intermediate Similarity	NPC313668
0.7091	Intermediate Similarity	NPC315836
0.7091	Intermediate Similarity	NPC77089
0.7087	Intermediate Similarity	NPC248574
0.7087	Intermediate Similarity	NPC108141
0.7083	Intermediate Similarity	NPC245094
0.7083	Intermediate Similarity	NPC311534
0.708	Intermediate Similarity	NPC110861
0.708	Intermediate Similarity	NPC475163
0.708	Intermediate Similarity	NPC181145
0.708	Intermediate Similarity	NPC261330
0.7075	Intermediate Similarity	NPC97435
0.7071	Intermediate Similarity	NPC241054
0.7069	Intermediate Similarity	NPC48692
0.7064	Intermediate Similarity	NPC202524
0.7064	Intermediate Similarity	NPC112780
0.7059	Intermediate Similarity	NPC320089
0.7059	Intermediate Similarity	NPC217901
0.7054	Intermediate Similarity	NPC11252
0.7054	Intermediate Similarity	NPC42658
0.7054	Intermediate Similarity	NPC289312
0.7054	Intermediate Similarity	NPC269530
0.7049	Intermediate Similarity	NPC231240
0.7048	Intermediate Similarity	NPC81483
0.7048	Intermediate Similarity	NPC264378
0.7048	Intermediate Similarity	NPC169468
0.7048	Intermediate Similarity	NPC40182
0.7048	Intermediate Similarity	NPC198422
0.7048	Intermediate Similarity	NPC161855
0.7048	Intermediate Similarity	NPC35717
0.7048	Intermediate Similarity	NPC307517
0.7048	Intermediate Similarity	NPC222303
0.7048	Intermediate Similarity	NPC61630
0.7048	Intermediate Similarity	NPC300584
0.7048	Intermediate Similarity	NPC56071
0.7048	Intermediate Similarity	NPC469565
0.7048	Intermediate Similarity	NPC70733
0.7037	Intermediate Similarity	NPC146731
0.7037	Intermediate Similarity	NPC472748
0.7037	Intermediate Similarity	NPC222161
0.7034	Intermediate Similarity	NPC91693
0.7034	Intermediate Similarity	NPC265557
0.7034	Intermediate Similarity	NPC18945
0.7034	Intermediate Similarity	NPC105926
0.7034	Intermediate Similarity	NPC67251
0.703	Intermediate Similarity	NPC477684
0.703	Intermediate Similarity	NPC469464
0.703	Intermediate Similarity	NPC316228
0.703	Intermediate Similarity	NPC202886
0.7027	Intermediate Similarity	NPC99760
0.7027	Intermediate Similarity	NPC83005
0.7027	Intermediate Similarity	NPC163314
0.7025	Intermediate Similarity	NPC471407
0.7025	Intermediate Similarity	NPC162495
0.7025	Intermediate Similarity	NPC473593
0.7019	Intermediate Similarity	NPC91439
0.7018	Intermediate Similarity	NPC235539
0.7018	Intermediate Similarity	NPC268954
0.7018	Intermediate Similarity	NPC44170
0.7018	Intermediate Similarity	NPC134869
0.7018	Intermediate Similarity	NPC152199
0.701	Intermediate Similarity	NPC2379
0.701	Intermediate Similarity	NPC31019
0.701	Intermediate Similarity	NPC106912
0.701	Intermediate Similarity	NPC66764
0.701	Intermediate Similarity	NPC110150
0.701	Intermediate Similarity	NPC185949
0.701	Intermediate Similarity	NPC27314
0.701	Intermediate Similarity	NPC263087
0.701	Intermediate Similarity	NPC107498
0.7009	Intermediate Similarity	NPC67569
0.7009	Intermediate Similarity	NPC478176
0.7009	Intermediate Similarity	NPC102822
0.7009	Intermediate Similarity	NPC471999
0.7009	Intermediate Similarity	NPC477046
0.7009	Intermediate Similarity	NPC170880
0.7009	Intermediate Similarity	NPC472000
0.7009	Intermediate Similarity	NPC165250
0.7	Intermediate Similarity	NPC475273
0.7	Intermediate Similarity	NPC325054
0.7	Intermediate Similarity	NPC264819
0.7	Intermediate Similarity	NPC471755
0.7	Intermediate Similarity	NPC168849
0.7	Intermediate Similarity	NPC471756
0.7	Intermediate Similarity	NPC269677
0.7	Intermediate Similarity	NPC472011

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 NPC227494 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1876
0.2-0.3	3813
0.3-0.4	2154
0.4-0.5	747
0.5-0.6	307
0.6-0.7	52
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.703	Intermediate Similarity	NPD46	Approved
0.703	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD8513	Phase 3
0.6964	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8517	Approved
0.6864	Remote Similarity	NPD8515	Approved
0.6864	Remote Similarity	NPD8516	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.681	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6054	Approved
0.678	Remote Similarity	NPD6059	Approved
0.6757	Remote Similarity	NPD6412	Phase 2
0.675	Remote Similarity	NPD8328	Phase 3
0.6729	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD6016	Approved
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6637	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7319	Approved
0.6585	Remote Similarity	NPD8074	Phase 3
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7492	Approved
0.6525	Remote Similarity	NPD6009	Approved
0.6509	Remote Similarity	NPD5282	Discontinued
0.6504	Remote Similarity	NPD7507	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD6053	Discontinued
0.646	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7078	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6435	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.641	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6325	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6371	Approved
0.6273	Remote Similarity	NPD4225	Approved
0.6271	Remote Similarity	NPD8133	Approved
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.626	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD7632	Discontinued
0.6228	Remote Similarity	NPD6402	Approved
0.6228	Remote Similarity	NPD6675	Approved
0.6228	Remote Similarity	NPD5739	Approved
0.6228	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD1696	Phase 3
0.621	Remote Similarity	NPD7642	Approved
0.6198	Remote Similarity	NPD7328	Approved
0.6198	Remote Similarity	NPD7327	Approved
0.6196	Remote Similarity	NPD3704	Approved
0.6182	Remote Similarity	NPD4755	Approved
0.6179	Remote Similarity	NPD7503	Approved
0.6179	Remote Similarity	NPD8033	Approved
0.6174	Remote Similarity	NPD5697	Approved
0.6174	Remote Similarity	NPD5701	Approved
0.6148	Remote Similarity	NPD7516	Approved
0.6132	Remote Similarity	NPD6101	Approved
0.6132	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7320	Approved
0.6121	Remote Similarity	NPD6881	Approved
0.6121	Remote Similarity	NPD6899	Approved
0.6121	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD5211	Phase 2
0.6098	Remote Similarity	NPD8377	Approved
0.6098	Remote Similarity	NPD8294	Approved
0.6091	Remote Similarity	NPD7839	Suspended
0.608	Remote Similarity	NPD7829	Approved
0.608	Remote Similarity	NPD7830	Approved
0.6075	Remote Similarity	NPD7838	Discovery
0.6071	Remote Similarity	NPD5285	Approved
0.6071	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD4696	Approved
0.6071	Remote Similarity	NPD4700	Approved
0.6068	Remote Similarity	NPD6372	Approved
0.6068	Remote Similarity	NPD6013	Approved
0.6068	Remote Similarity	NPD6373	Approved
0.6068	Remote Similarity	NPD6014	Approved
0.6068	Remote Similarity	NPD6012	Approved
0.6058	Remote Similarity	NPD1694	Approved
0.6055	Remote Similarity	NPD7748	Approved
0.605	Remote Similarity	NPD8297	Approved
0.6048	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8378	Approved
0.6048	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD8380	Approved
0.6048	Remote Similarity	NPD6921	Approved
0.6048	Remote Similarity	NPD8335	Approved
0.6048	Remote Similarity	NPD8379	Approved
0.6048	Remote Similarity	NPD8296	Approved
0.6047	Remote Similarity	NPD5956	Approved
0.604	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD7515	Phase 2
0.6018	Remote Similarity	NPD5223	Approved
0.6018	Remote Similarity	NPD5344	Discontinued
0.6017	Remote Similarity	NPD7102	Approved
0.6017	Remote Similarity	NPD7290	Approved
0.6017	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5141	Approved
0.5984	Remote Similarity	NPD7500	Approved
0.5981	Remote Similarity	NPD4753	Phase 2
0.5966	Remote Similarity	NPD6617	Approved
0.5966	Remote Similarity	NPD6869	Approved
0.5966	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6650	Approved
0.5966	Remote Similarity	NPD6847	Approved
0.5966	Remote Similarity	NPD6649	Approved
0.5966	Remote Similarity	NPD8130	Phase 1
0.5965	Remote Similarity	NPD5225	Approved
0.5965	Remote Similarity	NPD4633	Approved
0.5965	Remote Similarity	NPD5226	Approved
0.5965	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD6399	Phase 3
0.5963	Remote Similarity	NPD4202	Approved
0.5962	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6067	Discontinued
0.5952	Remote Similarity	NPD7604	Phase 2
0.5948	Remote Similarity	NPD6008	Approved
0.5946	Remote Similarity	NPD5222	Approved
0.5946	Remote Similarity	NPD4697	Phase 3
0.5946	Remote Similarity	NPD5221	Approved
0.5946	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.594	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.5922	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8444	Approved
0.5913	Remote Similarity	NPD5174	Approved
0.5913	Remote Similarity	NPD4754	Approved
0.5913	Remote Similarity	NPD5175	Approved
0.5896	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5173	Approved
0.5882	Remote Similarity	NPD4695	Discontinued
0.5878	Remote Similarity	NPD7260	Phase 2
0.5872	Remote Similarity	NPD5693	Phase 1
0.5865	Remote Similarity	NPD8415	Approved
0.5859	Remote Similarity	NPD8451	Approved
0.5859	Remote Similarity	NPD6336	Discontinued
0.5854	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5279	Phase 3
0.5849	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3617	Approved
0.5841	Remote Similarity	NPD5696	Approved
0.5833	Remote Similarity	NPD5328	Approved
0.5833	Remote Similarity	NPD6845	Suspended
0.5814	Remote Similarity	NPD8448	Approved
0.5812	Remote Similarity	NPD4768	Approved
0.5812	Remote Similarity	NPD4767	Approved
0.581	Remote Similarity	NPD4786	Approved
0.581	Remote Similarity	NPD3666	Approved
0.581	Remote Similarity	NPD3665	Phase 1
0.581	Remote Similarity	NPD3133	Approved
0.5802	Remote Similarity	NPD8392	Approved
0.5802	Remote Similarity	NPD8390	Approved
0.5802	Remote Similarity	NPD8391	Approved
0.5772	Remote Similarity	NPD6274	Approved
0.5766	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7900	Approved
0.576	Remote Similarity	NPD4522	Approved
0.5755	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5363	Approved
0.5745	Remote Similarity	NPD7341	Phase 2
0.5743	Remote Similarity	NPD4756	Discovery
0.5741	Remote Similarity	NPD6672	Approved
0.5741	Remote Similarity	NPD5737	Approved
0.5727	Remote Similarity	NPD6079	Approved
0.5726	Remote Similarity	NPD6317	Approved
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7331	Phase 2
0.5682	Remote Similarity	NPD6914	Discontinued
0.568	Remote Similarity	NPD6313	Approved
0.568	Remote Similarity	NPD6314	Approved
0.568	Remote Similarity	NPD7641	Discontinued
0.568	Remote Similarity	NPD6335	Approved
0.5673	Remote Similarity	NPD5369	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