NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	2.665
LogD:	2.662
LogS:	-4.041
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	5.1
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:	-4.712
MDCK Permeability:	2.289467738592066e-05
Pgp-inhibitor:	0.857
Pgp-substrate:	0.383
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.409
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.676
Plasma Protein Binding (PPB):	80.26765441894531%
Volume Distribution (VD):	1.767
Pgp-substrate:	21.24406623840332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.505
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.342
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	5.368
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.134
Carcinogencity:	0.021
Eye Corrosion:	0.01
Eye Irritation:	0.733
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: NPC476646

Natural Product ID:	NPC476646
*Common Name:**	Aspergiloid D
IUPAC Name:	(1S,2R,4aS,4bR,5R,8aS,9S)-2-ethenyl-2,4b,8,8-tetramethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthrene-1,5,9-triol
Synonyms:	Rel-Aspergiloid D
Standard InCHIKey:	OYKNTSVOOWIRJG-SEMYFXIOSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-6-19(4)10-7-13-12(17(19)23)11-14(21)16-18(2,3)9-8-15(22)20(13,16)5/h6,11,13-17,21-23H,1,7-10H2,2-5H3/t13-,14-,15+,16-,17+,19-,20-/m0/s1
SMILES:	C[C@@]1(CC[C@H]2C(=C[C@@H]([C@@H]3[C@@]2([C@@H](CCC3(C)C)O)C)O)[C@H]1O)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57333712
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO33649	Aspergillus sp. YXf3	Species	Aspergillaceae	Eukaryota	isolated from a healthy leaf of Ginkgo biloba	the campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	30000	nM	PMID[22196792]

☑ 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 NPC476646 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	188
0.1-0.2	1379
0.2-0.3	4777
0.3-0.4	12956
0.4-0.5	11518
0.5-0.6	6058
0.6-0.7	4239
0.7-0.8	1263
0.8-0.85	214
0.85-0.9	80
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC96362
0.9467	High Similarity	NPC91594
0.9467	High Similarity	NPC471798
0.9333	High Similarity	NPC253190
0.9231	High Similarity	NPC249423
0.92	High Similarity	NPC291503
0.9136	High Similarity	NPC261266
0.9114	High Similarity	NPC50964
0.9103	High Similarity	NPC287749
0.9091	High Similarity	NPC167891
0.9091	High Similarity	NPC83351
0.9079	High Similarity	NPC265588
0.9067	High Similarity	NPC306727
0.9067	High Similarity	NPC477138
0.9067	High Similarity	NPC243342
0.8987	High Similarity	NPC209620
0.8987	High Similarity	NPC23852
0.8961	High Similarity	NPC470711
0.8961	High Similarity	NPC470758
0.8961	High Similarity	NPC130136
0.8947	High Similarity	NPC32832
0.8933	High Similarity	NPC471799
0.8933	High Similarity	NPC182717
0.8929	High Similarity	NPC80561
0.8929	High Similarity	NPC11216
0.8929	High Similarity	NPC329596
0.8929	High Similarity	NPC204188
0.8929	High Similarity	NPC3345
0.8929	High Similarity	NPC291484
0.8916	High Similarity	NPC133588
0.8902	High Similarity	NPC6391
0.8902	High Similarity	NPC299068
0.8875	High Similarity	NPC49964
0.8861	High Similarity	NPC234193
0.8861	High Similarity	NPC295131
0.8846	High Similarity	NPC11908
0.8846	High Similarity	NPC476314
0.8831	High Similarity	NPC470749
0.8831	High Similarity	NPC106432
0.8824	High Similarity	NPC97404
0.8824	High Similarity	NPC41554
0.8816	High Similarity	NPC201048
0.8816	High Similarity	NPC91858
0.8816	High Similarity	NPC471797
0.8816	High Similarity	NPC476366
0.881	High Similarity	NPC470361
0.88	High Similarity	NPC242001
0.878	High Similarity	NPC470360
0.875	High Similarity	NPC264245
0.8734	High Similarity	NPC28862
0.8734	High Similarity	NPC47982
0.8734	High Similarity	NPC81306
0.8734	High Similarity	NPC109546
0.8734	High Similarity	NPC472463
0.8734	High Similarity	NPC143182
0.8734	High Similarity	NPC84694
0.8734	High Similarity	NPC30986
0.8734	High Similarity	NPC209430
0.8706	High Similarity	NPC295668
0.8701	High Similarity	NPC66566
0.8701	High Similarity	NPC477923
0.869	High Similarity	NPC474668
0.8675	High Similarity	NPC139724
0.8667	High Similarity	NPC34834
0.8667	High Similarity	NPC145498
0.8667	High Similarity	NPC92801
0.8659	High Similarity	NPC205845
0.8659	High Similarity	NPC124172
0.8642	High Similarity	NPC101462
0.8642	High Similarity	NPC248886
0.8642	High Similarity	NPC218616
0.8642	High Similarity	NPC296701
0.8642	High Similarity	NPC87489
0.8625	High Similarity	NPC241290
0.8625	High Similarity	NPC164840
0.8625	High Similarity	NPC209944
0.8608	High Similarity	NPC474989
0.8608	High Similarity	NPC148977
0.8608	High Similarity	NPC22955
0.8608	High Similarity	NPC99168
0.8608	High Similarity	NPC87604
0.8608	High Similarity	NPC474216
0.8608	High Similarity	NPC300499
0.8608	High Similarity	NPC470396
0.859	High Similarity	NPC274079
0.859	High Similarity	NPC477925
0.8588	High Similarity	NPC259875
0.8588	High Similarity	NPC16265
0.8588	High Similarity	NPC187785
0.8571	High Similarity	NPC100334
0.8554	High Similarity	NPC274448
0.8553	High Similarity	NPC110799
0.8553	High Similarity	NPC23954
0.8553	High Similarity	NPC167706
0.8537	High Similarity	NPC317458
0.8537	High Similarity	NPC477818
0.8519	High Similarity	NPC47761
0.8519	High Similarity	NPC470383
0.8519	High Similarity	NPC242350
0.8506	High Similarity	NPC310013
0.85	High Similarity	NPC291379
0.85	High Similarity	NPC53744
0.8488	Intermediate Similarity	NPC470390
0.8488	Intermediate Similarity	NPC245410
0.8488	Intermediate Similarity	NPC14380
0.8488	Intermediate Similarity	NPC192437
0.8488	Intermediate Similarity	NPC270511
0.8481	Intermediate Similarity	NPC40394
0.8481	Intermediate Similarity	NPC157996
0.8481	Intermediate Similarity	NPC472805
0.8481	Intermediate Similarity	NPC101475
0.8481	Intermediate Similarity	NPC34177
0.8481	Intermediate Similarity	NPC477924
0.8481	Intermediate Similarity	NPC90979
0.8452	Intermediate Similarity	NPC237344
0.8452	Intermediate Similarity	NPC24277
0.8452	Intermediate Similarity	NPC152808
0.8452	Intermediate Similarity	NPC293287
0.8442	Intermediate Similarity	NPC220939
0.8442	Intermediate Similarity	NPC68443
0.8442	Intermediate Similarity	NPC265485
0.8434	Intermediate Similarity	NPC127606
0.8434	Intermediate Similarity	NPC209802
0.8434	Intermediate Similarity	NPC470077
0.8434	Intermediate Similarity	NPC474493
0.8434	Intermediate Similarity	NPC475798
0.8434	Intermediate Similarity	NPC231310
0.8434	Intermediate Similarity	NPC185568
0.8434	Intermediate Similarity	NPC238485
0.8427	Intermediate Similarity	NPC288970
0.8415	Intermediate Similarity	NPC304285
0.8415	Intermediate Similarity	NPC470049
0.8415	Intermediate Similarity	NPC470614
0.8415	Intermediate Similarity	NPC1272
0.8415	Intermediate Similarity	NPC189972
0.8415	Intermediate Similarity	NPC202389
0.8409	Intermediate Similarity	NPC127718
0.8409	Intermediate Similarity	NPC65402
0.84	Intermediate Similarity	NPC96484
0.84	Intermediate Similarity	NPC471238
0.84	Intermediate Similarity	NPC208999
0.8395	Intermediate Similarity	NPC26117
0.8395	Intermediate Similarity	NPC47149
0.8375	Intermediate Similarity	NPC244385
0.8375	Intermediate Similarity	NPC167037
0.8375	Intermediate Similarity	NPC138621
0.8375	Intermediate Similarity	NPC253807
0.8375	Intermediate Similarity	NPC230295
0.8375	Intermediate Similarity	NPC158662
0.8375	Intermediate Similarity	NPC275910
0.8375	Intermediate Similarity	NPC98386
0.8375	Intermediate Similarity	NPC6978
0.8375	Intermediate Similarity	NPC473943
0.8375	Intermediate Similarity	NPC196753
0.8372	Intermediate Similarity	NPC101886
0.8372	Intermediate Similarity	NPC477917
0.8372	Intermediate Similarity	NPC115607
0.8354	Intermediate Similarity	NPC30590
0.8354	Intermediate Similarity	NPC247325
0.8354	Intermediate Similarity	NPC240604
0.8354	Intermediate Similarity	NPC106364
0.8354	Intermediate Similarity	NPC63958
0.8354	Intermediate Similarity	NPC244488
0.8354	Intermediate Similarity	NPC129165
0.8354	Intermediate Similarity	NPC321016
0.8354	Intermediate Similarity	NPC107059
0.8354	Intermediate Similarity	NPC120098
0.8354	Intermediate Similarity	NPC300324
0.8354	Intermediate Similarity	NPC27765
0.8354	Intermediate Similarity	NPC265328
0.8354	Intermediate Similarity	NPC189883
0.8354	Intermediate Similarity	NPC134330
0.8354	Intermediate Similarity	NPC122418
0.8354	Intermediate Similarity	NPC113733
0.8354	Intermediate Similarity	NPC321381
0.8354	Intermediate Similarity	NPC290598
0.8353	Intermediate Similarity	NPC149224
0.8353	Intermediate Similarity	NPC470620
0.8333	Intermediate Similarity	NPC469533
0.8333	Intermediate Similarity	NPC157257
0.8333	Intermediate Similarity	NPC266511
0.8333	Intermediate Similarity	NPC318390
0.8333	Intermediate Similarity	NPC469534
0.8333	Intermediate Similarity	NPC469593
0.8315	Intermediate Similarity	NPC8774
0.8313	Intermediate Similarity	NPC193870
0.8313	Intermediate Similarity	NPC141941
0.8313	Intermediate Similarity	NPC474634
0.8313	Intermediate Similarity	NPC237795
0.8313	Intermediate Similarity	NPC82623
0.8313	Intermediate Similarity	NPC110778
0.8313	Intermediate Similarity	NPC470384
0.8313	Intermediate Similarity	NPC475789
0.8313	Intermediate Similarity	NPC82538
0.8312	Intermediate Similarity	NPC477792
0.8312	Intermediate Similarity	NPC471272
0.8312	Intermediate Similarity	NPC164022
0.8293	Intermediate Similarity	NPC474752
0.8293	Intermediate Similarity	NPC7505
0.8293	Intermediate Similarity	NPC142163

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 NPC476646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1615
0.2-0.3	3946
0.3-0.4	2224
0.4-0.5	758
0.5-0.6	232
0.6-0.7	153
0.7-0.8	39
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD7645	Phase 2
0.8228	Intermediate Similarity	NPD6942	Approved
0.8228	Intermediate Similarity	NPD7339	Approved
0.8228	Intermediate Similarity	NPD8264	Approved
0.8171	Intermediate Similarity	NPD7525	Registered
0.814	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6929	Approved
0.7738	Intermediate Similarity	NPD6931	Approved
0.7738	Intermediate Similarity	NPD7514	Phase 3
0.7738	Intermediate Similarity	NPD7332	Phase 2
0.7738	Intermediate Similarity	NPD6930	Phase 2
0.7711	Intermediate Similarity	NPD7145	Approved
0.7647	Intermediate Similarity	NPD6902	Approved
0.759	Intermediate Similarity	NPD5776	Phase 2
0.759	Intermediate Similarity	NPD6925	Approved
0.7586	Intermediate Similarity	NPD4786	Approved
0.7586	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6695	Phase 3
0.7439	Intermediate Similarity	NPD4784	Approved
0.7439	Intermediate Similarity	NPD6924	Approved
0.7439	Intermediate Similarity	NPD6926	Approved
0.7439	Intermediate Similarity	NPD4785	Approved
0.7416	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD7152	Approved
0.7407	Intermediate Similarity	NPD7151	Approved
0.7407	Intermediate Similarity	NPD7150	Approved
0.7396	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD7640	Approved
0.7391	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD6932	Approved
0.7368	Intermediate Similarity	NPD368	Approved
0.7363	Intermediate Similarity	NPD5328	Approved
0.7326	Intermediate Similarity	NPD7509	Discontinued
0.7303	Intermediate Similarity	NPD6893	Approved
0.7292	Intermediate Similarity	NPD7638	Approved
0.7284	Intermediate Similarity	NPD7144	Approved
0.7284	Intermediate Similarity	NPD7143	Approved
0.7262	Intermediate Similarity	NPD6933	Approved
0.7241	Intermediate Similarity	NPD6898	Phase 1
0.7204	Intermediate Similarity	NPD7515	Phase 2
0.7195	Intermediate Similarity	NPD4243	Approved
0.716	Intermediate Similarity	NPD6922	Approved
0.716	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7143	Intermediate Similarity	NPD7524	Approved
0.7128	Intermediate Similarity	NPD4202	Approved
0.7126	Intermediate Similarity	NPD4748	Discontinued
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7011	Intermediate Similarity	NPD6683	Phase 2
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6931	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD5221	Approved
0.6907	Remote Similarity	NPD5222	Approved
0.6907	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD5285	Approved
0.6869	Remote Similarity	NPD5286	Approved
0.6869	Remote Similarity	NPD4696	Approved
0.6848	Remote Similarity	NPD4623	Approved
0.6848	Remote Similarity	NPD4519	Discontinued
0.6842	Remote Similarity	NPD7087	Discontinued
0.6842	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD5173	Approved
0.6837	Remote Similarity	NPD7902	Approved
0.6837	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.68	Remote Similarity	NPD5223	Approved
0.68	Remote Similarity	NPD342	Phase 1
0.6771	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5290	Discontinued
0.6768	Remote Similarity	NPD4225	Approved
0.6744	Remote Similarity	NPD4190	Phase 3
0.6744	Remote Similarity	NPD5275	Approved
0.6739	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7136	Phase 2
0.6735	Remote Similarity	NPD4697	Phase 3
0.6733	Remote Similarity	NPD4633	Approved
0.6733	Remote Similarity	NPD7632	Discontinued
0.6733	Remote Similarity	NPD5224	Approved
0.6733	Remote Similarity	NPD5225	Approved
0.6733	Remote Similarity	NPD5226	Approved
0.6706	Remote Similarity	NPD4732	Discontinued
0.67	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6556	Remote Similarity	NPD4695	Discontinued
0.6545	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7900	Approved
0.6505	Remote Similarity	NPD4754	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6494	Remote Similarity	NPD4219	Approved
0.6489	Remote Similarity	NPD5279	Phase 3
0.6476	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD4159	Approved
0.6458	Remote Similarity	NPD6051	Approved
0.6458	Remote Similarity	NPD4753	Phase 2
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6422	Remote Similarity	NPD4632	Approved
0.6415	Remote Similarity	NPD6011	Approved
0.6415	Remote Similarity	NPD4729	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD4730	Approved
0.6413	Remote Similarity	NPD4223	Phase 3
0.6413	Remote Similarity	NPD4221	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6389	Remote Similarity	NPD6617	Approved
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6649	Approved
0.6383	Remote Similarity	NPD1696	Phase 3
0.6383	Remote Similarity	NPD5329	Approved
0.6381	Remote Similarity	NPD4767	Approved
0.6381	Remote Similarity	NPD4768	Approved
0.6374	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6648	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6353	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7327	Approved
0.6339	Remote Similarity	NPD7328	Approved
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD8034	Phase 2
0.6327	Remote Similarity	NPD8035	Phase 2
0.6321	Remote Similarity	NPD6412	Phase 2
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD8033	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD7503	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5210	Approved
0.63	Remote Similarity	NPD4629	Approved
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5169	Approved
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD5250	Approved
0.6296	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5135	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD7516	Approved
0.6277	Remote Similarity	NPD4197	Approved
0.6262	Remote Similarity	NPD5128	Approved
0.6262	Remote Similarity	NPD5168	Approved
0.6262	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD5127	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5215	Approved
0.6239	Remote Similarity	NPD5216	Approved
0.6239	Remote Similarity	NPD5217	Approved
0.6228	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD8294	Approved
0.6226	Remote Similarity	NPD6008	Approved
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4822	Approved
0.6196	Remote Similarity	NPD4821	Approved
0.6196	Remote Similarity	NPD4819	Approved
0.6196	Remote Similarity	NPD4820	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6903	Approved
0.618	Remote Similarity	NPD3703	Phase 2
0.6176	Remote Similarity	NPD6083	Phase 2
0.6176	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD8380	Approved
0.6174	Remote Similarity	NPD8335	Approved
0.6174	Remote Similarity	NPD8379	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