NPASS Compound

Structure

NPC206 OpenBabel07101718242D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 21 4 1 1 0 0 0 22 5 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	5.304
LogD:	4.332
LogS:	-4.086
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	4.034
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.759
MDCK Permeability:	1.9246628653490916e-05
Pgp-inhibitor:	0.445
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	97.31022644042969%
Volume Distribution (VD):	1.455
Pgp-substrate:	2.4598073959350586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.683
CYP2D6-substrate:	0.8
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	11.337
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.936
Carcinogencity:	0.05
Eye Corrosion:	0.407
Eye Irritation:	0.917
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC206

Natural Product ID:	NPC206
*Common Name:**	Albaconol
IUPAC Name:	2-[[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-methylbenzene-1,3-diol
Synonyms:	Albaconol
Standard InCHIKey:	APLGGFLATUGFCO-YUVXSKOASA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-14-11-16(23)15(17(24)12-14)13-19-21(4)9-6-8-20(2,3)18(21)7-10-22(19,5)25/h11-12,18-19,23-25H,6-10,13H2,1-5H3/t18-,19+,21-,22+/m0/s1
SMILES:	Cc1cc(c(C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)O)c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512488
PubChem CID:	5317148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO27473	Albatrellus confluens	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27473	Albatrellus confluens	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27473	Albatrellus confluens	Species	Albatrellaceae	Eukaryota	n.a.	Yunnan, China	n.a.	Database[Title]
NPO27473	Albatrellus confluens	Species	Albatrellaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	IC50	=	5000.0	nM	PMID[506840]

☑ 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 NPC206 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	375
0.1-0.2	1626
0.2-0.3	3588
0.3-0.4	8576
0.4-0.5	10833
0.5-0.6	9272
0.6-0.7	6958
0.7-0.8	1290
0.8-0.85	144
0.85-0.9	31
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC246760
0.9375	High Similarity	NPC84999
0.9123	High Similarity	NPC141001
0.9027	High Similarity	NPC263753
0.9027	High Similarity	NPC23804
0.9018	High Similarity	NPC224527
0.9009	High Similarity	NPC186385
0.9009	High Similarity	NPC299568
0.8957	High Similarity	NPC471668
0.8938	High Similarity	NPC166995
0.8909	High Similarity	NPC99836
0.8909	High Similarity	NPC12640
0.8909	High Similarity	NPC201662
0.8879	High Similarity	NPC172219
0.8879	High Similarity	NPC304510
0.886	High Similarity	NPC117846
0.885	High Similarity	NPC176279
0.885	High Similarity	NPC260323
0.8839	High Similarity	NPC19808
0.8839	High Similarity	NPC33728
0.8829	High Similarity	NPC158253
0.8829	High Similarity	NPC232523
0.8829	High Similarity	NPC204901
0.8818	High Similarity	NPC37802
0.8803	High Similarity	NPC471671
0.8793	High Similarity	NPC115808
0.8783	High Similarity	NPC471534
0.8783	High Similarity	NPC107240
0.8761	High Similarity	NPC224870
0.875	High Similarity	NPC174981
0.8729	High Similarity	NPC126002
0.8729	High Similarity	NPC469644
0.8729	High Similarity	NPC93071
0.8727	High Similarity	NPC218879
0.8727	High Similarity	NPC244513
0.8727	High Similarity	NPC227458
0.8718	High Similarity	NPC470760
0.8707	High Similarity	NPC35797
0.8707	High Similarity	NPC192948
0.8696	High Similarity	NPC319803
0.8684	High Similarity	NPC77772
0.8684	High Similarity	NPC165770
0.8684	High Similarity	NPC4493
0.8684	High Similarity	NPC225679
0.8684	High Similarity	NPC476632
0.8655	High Similarity	NPC69006
0.8644	High Similarity	NPC48781
0.8644	High Similarity	NPC9592
0.8632	High Similarity	NPC38893
0.8632	High Similarity	NPC477137
0.8632	High Similarity	NPC308311
0.8621	High Similarity	NPC195922
0.8621	High Similarity	NPC249270
0.8609	High Similarity	NPC43525
0.8609	High Similarity	NPC62867
0.8609	High Similarity	NPC250323
0.8609	High Similarity	NPC177962
0.8607	High Similarity	NPC224342
0.8596	High Similarity	NPC141782
0.8547	High Similarity	NPC469719
0.8545	High Similarity	NPC192032
0.8545	High Similarity	NPC166313
0.8545	High Similarity	NPC294186
0.8545	High Similarity	NPC147310
0.8545	High Similarity	NPC11280
0.8545	High Similarity	NPC24407
0.8545	High Similarity	NPC137415
0.8525	High Similarity	NPC53567
0.8522	High Similarity	NPC469912
0.8522	High Similarity	NPC151537
0.8522	High Similarity	NPC470770
0.8522	High Similarity	NPC266937
0.8512	High Similarity	NPC39029
0.8496	Intermediate Similarity	NPC151477
0.8487	Intermediate Similarity	NPC154030
0.8487	Intermediate Similarity	NPC469609
0.8482	Intermediate Similarity	NPC246056
0.8482	Intermediate Similarity	NPC117115
0.8482	Intermediate Similarity	NPC134829
0.8475	Intermediate Similarity	NPC469663
0.8475	Intermediate Similarity	NPC219112
0.8475	Intermediate Similarity	NPC92
0.8468	Intermediate Similarity	NPC302219
0.8468	Intermediate Similarity	NPC222522
0.8468	Intermediate Similarity	NPC85479
0.8468	Intermediate Similarity	NPC146798
0.8468	Intermediate Similarity	NPC168303
0.8468	Intermediate Similarity	NPC249828
0.8468	Intermediate Similarity	NPC53051
0.8468	Intermediate Similarity	NPC94351
0.8468	Intermediate Similarity	NPC24404
0.8468	Intermediate Similarity	NPC313030
0.8468	Intermediate Similarity	NPC106396
0.8468	Intermediate Similarity	NPC71002
0.8468	Intermediate Similarity	NPC242342
0.8462	Intermediate Similarity	NPC268160
0.8448	Intermediate Similarity	NPC473521
0.8448	Intermediate Similarity	NPC46940
0.8435	Intermediate Similarity	NPC13482
0.843	Intermediate Similarity	NPC24125
0.8421	Intermediate Similarity	NPC61885
0.8421	Intermediate Similarity	NPC11554
0.8421	Intermediate Similarity	NPC63698
0.8417	Intermediate Similarity	NPC151197
0.8417	Intermediate Similarity	NPC191866
0.8413	Intermediate Similarity	NPC222108
0.8413	Intermediate Similarity	NPC96719
0.8407	Intermediate Similarity	NPC39664
0.8407	Intermediate Similarity	NPC118286
0.8407	Intermediate Similarity	NPC470700
0.8407	Intermediate Similarity	NPC248904
0.8407	Intermediate Similarity	NPC302681
0.8407	Intermediate Similarity	NPC39097
0.8407	Intermediate Similarity	NPC109691
0.8403	Intermediate Similarity	NPC477136
0.8393	Intermediate Similarity	NPC241891
0.8393	Intermediate Similarity	NPC102216
0.839	Intermediate Similarity	NPC147179
0.8378	Intermediate Similarity	NPC72947
0.8378	Intermediate Similarity	NPC284011
0.8378	Intermediate Similarity	NPC252105
0.8376	Intermediate Similarity	NPC715
0.8376	Intermediate Similarity	NPC261343
0.8362	Intermediate Similarity	NPC322753
0.8362	Intermediate Similarity	NPC95716
0.8361	Intermediate Similarity	NPC237667
0.8359	Intermediate Similarity	NPC469611
0.8348	Intermediate Similarity	NPC202647
0.8333	Intermediate Similarity	NPC144343
0.8333	Intermediate Similarity	NPC320439
0.8333	Intermediate Similarity	NPC54844
0.832	Intermediate Similarity	NPC145659
0.832	Intermediate Similarity	NPC170485
0.832	Intermediate Similarity	NPC9292
0.8319	Intermediate Similarity	NPC219286
0.8319	Intermediate Similarity	NPC474839
0.8319	Intermediate Similarity	NPC99557
0.8319	Intermediate Similarity	NPC308828
0.8295	Intermediate Similarity	NPC469610
0.8293	Intermediate Similarity	NPC120172
0.8293	Intermediate Similarity	NPC122175
0.8293	Intermediate Similarity	NPC71094
0.8293	Intermediate Similarity	NPC478058
0.8291	Intermediate Similarity	NPC228425
0.8288	Intermediate Similarity	NPC10588
0.8288	Intermediate Similarity	NPC166761
0.8288	Intermediate Similarity	NPC72729
0.8281	Intermediate Similarity	NPC8899
0.8279	Intermediate Similarity	NPC328504
0.8276	Intermediate Similarity	NPC132720
0.8264	Intermediate Similarity	NPC217174
0.8261	Intermediate Similarity	NPC306295
0.8254	Intermediate Similarity	NPC471077
0.8254	Intermediate Similarity	NPC108164
0.825	Intermediate Similarity	NPC16030
0.825	Intermediate Similarity	NPC277588
0.8246	Intermediate Similarity	NPC53740
0.8246	Intermediate Similarity	NPC469913
0.8246	Intermediate Similarity	NPC21594
0.824	Intermediate Similarity	NPC124030
0.824	Intermediate Similarity	NPC105031
0.823	Intermediate Similarity	NPC30506
0.823	Intermediate Similarity	NPC119860
0.8226	Intermediate Similarity	NPC96940
0.8217	Intermediate Similarity	NPC472798
0.8214	Intermediate Similarity	NPC143659
0.8214	Intermediate Similarity	NPC100340
0.8211	Intermediate Similarity	NPC249340
0.8211	Intermediate Similarity	NPC162935
0.8198	Intermediate Similarity	NPC33675
0.8198	Intermediate Similarity	NPC299762
0.8197	Intermediate Similarity	NPC260832
0.8197	Intermediate Similarity	NPC223451
0.8197	Intermediate Similarity	NPC135467
0.819	Intermediate Similarity	NPC58865
0.8189	Intermediate Similarity	NPC215300
0.8182	Intermediate Similarity	NPC190514
0.8175	Intermediate Similarity	NPC325294
0.8175	Intermediate Similarity	NPC82299
0.8175	Intermediate Similarity	NPC321822
0.8175	Intermediate Similarity	NPC43000
0.8175	Intermediate Similarity	NPC100414
0.8174	Intermediate Similarity	NPC61033
0.8174	Intermediate Similarity	NPC305603
0.8174	Intermediate Similarity	NPC66834
0.816	Intermediate Similarity	NPC139774
0.816	Intermediate Similarity	NPC97578
0.816	Intermediate Similarity	NPC228503
0.816	Intermediate Similarity	NPC174729
0.816	Intermediate Similarity	NPC138248
0.8158	Intermediate Similarity	NPC292452
0.8158	Intermediate Similarity	NPC47284
0.8145	Intermediate Similarity	NPC471794
0.8145	Intermediate Similarity	NPC11250
0.814	Intermediate Similarity	NPC472590
0.814	Intermediate Similarity	NPC160623
0.814	Intermediate Similarity	NPC471517
0.813	Intermediate Similarity	NPC259703
0.813	Intermediate Similarity	NPC32322
0.8125	Intermediate Similarity	NPC16577

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 NPC206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	916
0.2-0.3	1442
0.3-0.4	3035
0.4-0.5	1983
0.5-0.6	1077
0.6-0.7	289
0.7-0.8	55
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9009	High Similarity	NPD4750	Phase 3
0.8346	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD4749	Approved
0.8214	Intermediate Similarity	NPD940	Approved
0.8214	Intermediate Similarity	NPD846	Approved
0.8136	Intermediate Similarity	NPD7635	Approved
0.8125	Intermediate Similarity	NPD4625	Phase 3
0.8049	Intermediate Similarity	NPD4059	Approved
0.8045	Intermediate Similarity	NPD6099	Approved
0.8045	Intermediate Similarity	NPD6100	Approved
0.8033	Intermediate Similarity	NPD3091	Approved
0.8018	Intermediate Similarity	NPD288	Approved
0.8017	Intermediate Similarity	NPD2342	Discontinued
0.7965	Intermediate Similarity	NPD1242	Phase 1
0.7928	Intermediate Similarity	NPD844	Approved
0.792	Intermediate Similarity	NPD3092	Approved
0.7903	Intermediate Similarity	NPD3019	Approved
0.7876	Intermediate Similarity	NPD3020	Approved
0.7812	Intermediate Similarity	NPD3094	Phase 2
0.7807	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD1809	Phase 2
0.776	Intermediate Similarity	NPD2932	Approved
0.7681	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD3095	Discontinued
0.7611	Intermediate Similarity	NPD2859	Approved
0.7611	Intermediate Similarity	NPD2860	Approved
0.7597	Intermediate Similarity	NPD6696	Suspended
0.7589	Intermediate Similarity	NPD845	Approved
0.7583	Intermediate Similarity	NPD3022	Approved
0.7583	Intermediate Similarity	NPD3021	Approved
0.7574	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5736	Approved
0.7556	Intermediate Similarity	NPD4097	Suspended
0.7522	Intermediate Similarity	NPD2933	Approved
0.7522	Intermediate Similarity	NPD2934	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7402	Intermediate Similarity	NPD4093	Discontinued
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7364	Intermediate Similarity	NPD1201	Approved
0.7348	Intermediate Similarity	NPD4624	Approved
0.7344	Intermediate Similarity	NPD2286	Discontinued
0.7344	Intermediate Similarity	NPD1751	Approved
0.7333	Intermediate Similarity	NPD6663	Approved
0.7317	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1792	Phase 2
0.7287	Intermediate Similarity	NPD3023	Approved
0.7287	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD3024	Approved
0.7252	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2605	Approved
0.7239	Intermediate Similarity	NPD2606	Approved
0.7231	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6671	Approved
0.7214	Intermediate Similarity	NPD4726	Approved
0.7214	Intermediate Similarity	NPD4725	Approved
0.7214	Intermediate Similarity	NPD4721	Approved
0.72	Intermediate Similarity	NPD2229	Approved
0.72	Intermediate Similarity	NPD2234	Approved
0.72	Intermediate Similarity	NPD2228	Approved
0.72	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7741	Discontinued
0.7188	Intermediate Similarity	NPD1548	Phase 1
0.7185	Intermediate Similarity	NPD5156	Approved
0.7185	Intermediate Similarity	NPD5155	Approved
0.7165	Intermediate Similarity	NPD7340	Approved
0.7164	Intermediate Similarity	NPD3637	Approved
0.7164	Intermediate Similarity	NPD3635	Approved
0.7164	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3636	Approved
0.7153	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7121	Intermediate Similarity	NPD5327	Phase 3
0.7111	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3594	Approved
0.7111	Intermediate Similarity	NPD3595	Approved
0.7101	Intermediate Similarity	NPD5735	Approved
0.709	Intermediate Similarity	NPD2195	Approved
0.709	Intermediate Similarity	NPD2194	Approved
0.7077	Intermediate Similarity	NPD4589	Approved
0.7077	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD7743	Approved
0.7071	Intermediate Similarity	NPD7742	Approved
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7054	Intermediate Similarity	NPD7330	Discontinued
0.705	Intermediate Similarity	NPD6353	Approved
0.7049	Intermediate Similarity	NPD1444	Approved
0.7049	Intermediate Similarity	NPD1445	Approved
0.7037	Intermediate Similarity	NPD2861	Phase 2
0.7029	Intermediate Similarity	NPD2238	Phase 2
0.7008	Intermediate Similarity	NPD497	Approved
0.6929	Remote Similarity	NPD498	Approved
0.6929	Remote Similarity	NPD496	Approved
0.6929	Remote Similarity	NPD1398	Phase 1
0.6929	Remote Similarity	NPD495	Approved
0.6923	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5304	Approved
0.6923	Remote Similarity	NPD5303	Approved
0.6917	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD2233	Approved
0.6917	Remote Similarity	NPD2232	Approved
0.6906	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1613	Approved
0.6906	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD111	Approved
0.6875	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD422	Phase 1
0.6828	Remote Similarity	NPD8166	Discontinued
0.6818	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9093	Approved
0.6812	Remote Similarity	NPD7095	Approved
0.6803	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4060	Phase 1
0.6786	Remote Similarity	NPD943	Approved
0.6781	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD37	Approved
0.6769	Remote Similarity	NPD7636	Approved
0.6761	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3638	Discontinued
0.6759	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD9089	Approved
0.6757	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1791	Approved
0.6744	Remote Similarity	NPD1793	Approved
0.6742	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5691	Approved
0.673	Remote Similarity	NPD7473	Discontinued
0.6714	Remote Similarity	NPD6407	Approved
0.6714	Remote Similarity	NPD8032	Phase 2
0.6714	Remote Similarity	NPD6405	Approved
0.6712	Remote Similarity	NPD7003	Approved
0.6691	Remote Similarity	NPD8651	Approved
0.6691	Remote Similarity	NPD1283	Approved
0.669	Remote Similarity	NPD970	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4257	Approved
0.669	Remote Similarity	NPD2568	Approved
0.669	Remote Similarity	NPD1607	Approved
0.669	Remote Similarity	NPD4256	Phase 2
0.6689	Remote Similarity	NPD7041	Phase 2
0.6689	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD9500	Approved
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD5283	Phase 1
0.6646	Remote Similarity	NPD6232	Discontinued
0.6645	Remote Similarity	NPD4965	Approved
0.6645	Remote Similarity	NPD4966	Approved
0.6645	Remote Similarity	NPD4967	Phase 2
0.6644	Remote Similarity	NPD7447	Phase 1
0.6644	Remote Similarity	NPD6674	Discontinued
0.6643	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2797	Approved
0.6642	Remote Similarity	NPD4103	Phase 2
0.6642	Remote Similarity	NPD3143	Discontinued
0.6642	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3028	Approved
0.6621	Remote Similarity	NPD5763	Approved
0.6621	Remote Similarity	NPD5762	Approved
0.662	Remote Similarity	NPD5124	Phase 1
0.662	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4659	Approved
0.6617	Remote Similarity	NPD1651	Approved
0.6615	Remote Similarity	NPD5951	Approved
0.6612	Remote Similarity	NPD9273	Approved
0.6599	Remote Similarity	NPD3750	Approved
0.6599	Remote Similarity	NPD3892	Phase 2
0.6599	Remote Similarity	NPD7466	Approved
0.6594	Remote Similarity	NPD858	Approved
0.6594	Remote Similarity	NPD602	Approved
0.6594	Remote Similarity	NPD599	Approved
0.6594	Remote Similarity	NPD6584	Phase 3
0.6594	Remote Similarity	NPD859	Approved
0.6582	Remote Similarity	NPD6959	Discontinued
0.6581	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7725	Approved
0.6567	Remote Similarity	NPD1778	Approved
0.6567	Remote Similarity	NPD2668	Approved
0.6567	Remote Similarity	NPD2667	Approved
0.6565	Remote Similarity	NPD4198	Discontinued
0.6565	Remote Similarity	NPD709	Approved
0.6565	Remote Similarity	NPD7157	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