NPASS Compound

Structure

NPC204582 OpenBabel07101718322D 28 28 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 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 -5.1962 6.0000 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 -0.8660 -1.5000 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 -4.3301 4.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 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 -6.9282 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 7.5000 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 -3.4641 -1.0000 0.0000 O 0 0 0 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 -6.9282 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 6 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	417.434
LogP:	3.787
LogD:	1.746
LogS:	-3.435
# Rotatable Bonds:	10
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	3.847
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.183
MDCK Permeability:	1.2491177585616242e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.574
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	99.05236053466797%
Volume Distribution (VD):	0.276
Pgp-substrate:	1.8144038915634155%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	2.97
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.834
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.097
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC204582

Natural Product ID:	NPC204582
*Common Name:**	(+)-Monocycloalternarene B
IUPAC Name:	3-[(2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl]-4,5-dihydroxybenzoic acid
Synonyms:
Standard InCHIKey:	HEKKNGJOTDHUHQ-IJEFQKSISA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-14(6-5-7-15(2)9-11-19(24)22(3,4)28)8-10-16-12-17(21(26)27)13-18(23)20(16)25/h7-8,12-13,19,23-25,28H,5-6,9-11H2,1-4H3,(H,26,27)/b14-8+,15-7+/t19-/m1/s1
SMILES:	C/C(=CCc1cc(cc(c1O)O)C(=O)O)/CC/C=C(C)/CC[C@H](C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431890
PubChem CID:	72704675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32811	Alternaria sp. JJY-32	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128115]

☑ 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	=	47000.0	nM	PMID[523138]

☑ 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 NPC204582 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	291
0.1-0.2	1171
0.2-0.3	3102
0.3-0.4	7581
0.4-0.5	11573
0.5-0.6	4763
0.6-0.7	9545
0.7-0.8	4474
0.8-0.85	169
0.85-0.9	24
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC475111
0.9167	High Similarity	NPC239855
0.9055	High Similarity	NPC475192
0.8872	High Similarity	NPC473777
0.8779	High Similarity	NPC476022
0.8779	High Similarity	NPC474945
0.8696	High Similarity	NPC112135
0.8667	High Similarity	NPC302844
0.8662	High Similarity	NPC258856
0.8662	High Similarity	NPC75295
0.8657	High Similarity	NPC163169
0.8657	High Similarity	NPC123
0.8647	High Similarity	NPC473744
0.8594	High Similarity	NPC156654
0.8592	High Similarity	NPC469683
0.8582	High Similarity	NPC226855
0.8571	High Similarity	NPC471853
0.8571	High Similarity	NPC158654
0.8551	High Similarity	NPC156892
0.8521	High Similarity	NPC469615
0.8516	High Similarity	NPC273282
0.8516	High Similarity	NPC474890
0.8516	High Similarity	NPC161943
0.8504	High Similarity	NPC83718
0.8496	Intermediate Similarity	NPC474944
0.8478	Intermediate Similarity	NPC18646
0.8467	Intermediate Similarity	NPC471749
0.8462	Intermediate Similarity	NPC213900
0.8451	Intermediate Similarity	NPC248068
0.845	Intermediate Similarity	NPC473767
0.8446	Intermediate Similarity	NPC62051
0.844	Intermediate Similarity	NPC469911
0.844	Intermediate Similarity	NPC327187
0.8417	Intermediate Similarity	NPC326847
0.837	Intermediate Similarity	NPC476024
0.8358	Intermediate Similarity	NPC473751
0.8345	Intermediate Similarity	NPC176102
0.8345	Intermediate Similarity	NPC204257
0.8345	Intermediate Similarity	NPC229638
0.8345	Intermediate Similarity	NPC267539
0.8345	Intermediate Similarity	NPC29317
0.8345	Intermediate Similarity	NPC254832
0.8345	Intermediate Similarity	NPC71108
0.8333	Intermediate Similarity	NPC1321
0.8333	Intermediate Similarity	NPC304929
0.8333	Intermediate Similarity	NPC200422
0.8333	Intermediate Similarity	NPC157478
0.8333	Intermediate Similarity	NPC295406
0.8333	Intermediate Similarity	NPC289572
0.8333	Intermediate Similarity	NPC113397
0.8333	Intermediate Similarity	NPC225710
0.8333	Intermediate Similarity	NPC156124
0.8321	Intermediate Similarity	NPC264145
0.8311	Intermediate Similarity	NPC124842
0.8309	Intermediate Similarity	NPC474546
0.8299	Intermediate Similarity	NPC142654
0.8296	Intermediate Similarity	NPC209959
0.8295	Intermediate Similarity	NPC150919
0.8286	Intermediate Similarity	NPC65005
0.8286	Intermediate Similarity	NPC194764
0.8286	Intermediate Similarity	NPC264112
0.8284	Intermediate Similarity	NPC472592
0.8281	Intermediate Similarity	NPC4665
0.8273	Intermediate Similarity	NPC293454
0.8271	Intermediate Similarity	NPC174991
0.8264	Intermediate Similarity	NPC50954
0.8261	Intermediate Similarity	NPC111888
0.8252	Intermediate Similarity	NPC184053
0.8239	Intermediate Similarity	NPC75763
0.8239	Intermediate Similarity	NPC474875
0.8239	Intermediate Similarity	NPC476820
0.8239	Intermediate Similarity	NPC295492
0.8239	Intermediate Similarity	NPC225036
0.8239	Intermediate Similarity	NPC205751
0.8239	Intermediate Similarity	NPC105525
0.8239	Intermediate Similarity	NPC12218
0.8239	Intermediate Similarity	NPC303683
0.8239	Intermediate Similarity	NPC274891
0.8239	Intermediate Similarity	NPC26241
0.8239	Intermediate Similarity	NPC476819
0.8231	Intermediate Similarity	NPC63126
0.8219	Intermediate Similarity	NPC229264
0.8219	Intermediate Similarity	NPC473023
0.8209	Intermediate Similarity	NPC117794
0.8209	Intermediate Similarity	NPC85565
0.8209	Intermediate Similarity	NPC184219
0.8207	Intermediate Similarity	NPC126707
0.8207	Intermediate Similarity	NPC275278
0.8201	Intermediate Similarity	NPC159418
0.8201	Intermediate Similarity	NPC283823
0.8195	Intermediate Similarity	NPC297193
0.8195	Intermediate Similarity	NPC67300
0.8194	Intermediate Similarity	NPC184935
0.8188	Intermediate Similarity	NPC221249
0.8182	Intermediate Similarity	NPC476534
0.8175	Intermediate Similarity	NPC94810
0.8169	Intermediate Similarity	NPC230811
0.8169	Intermediate Similarity	NPC142703
0.8169	Intermediate Similarity	NPC175552
0.8169	Intermediate Similarity	NPC219428
0.8169	Intermediate Similarity	NPC141368
0.8169	Intermediate Similarity	NPC302857
0.8169	Intermediate Similarity	NPC152942
0.8169	Intermediate Similarity	NPC239943
0.8169	Intermediate Similarity	NPC37250
0.8169	Intermediate Similarity	NPC278068
0.8163	Intermediate Similarity	NPC472969
0.8162	Intermediate Similarity	NPC214620
0.8151	Intermediate Similarity	NPC473867
0.8143	Intermediate Similarity	NPC202225
0.8138	Intermediate Similarity	NPC50221
0.8138	Intermediate Similarity	NPC226738
0.8138	Intermediate Similarity	NPC190587
0.8138	Intermediate Similarity	NPC114242
0.8138	Intermediate Similarity	NPC473090
0.8138	Intermediate Similarity	NPC121573
0.8138	Intermediate Similarity	NPC22176
0.8125	Intermediate Similarity	NPC472904
0.8125	Intermediate Similarity	NPC477278
0.8125	Intermediate Similarity	NPC477277
0.812	Intermediate Similarity	NPC322332
0.8112	Intermediate Similarity	NPC472903
0.8112	Intermediate Similarity	NPC471819
0.8108	Intermediate Similarity	NPC98809
0.8108	Intermediate Similarity	NPC476394
0.8102	Intermediate Similarity	NPC229894
0.8102	Intermediate Similarity	NPC247250
0.8102	Intermediate Similarity	NPC767
0.8099	Intermediate Similarity	NPC170742
0.8099	Intermediate Similarity	NPC477592
0.8095	Intermediate Similarity	NPC474991
0.8095	Intermediate Similarity	NPC268366
0.8088	Intermediate Similarity	NPC110211
0.8088	Intermediate Similarity	NPC204579
0.8082	Intermediate Similarity	NPC105213
0.8082	Intermediate Similarity	NPC469854
0.8082	Intermediate Similarity	NPC469856
0.8074	Intermediate Similarity	NPC469568
0.8071	Intermediate Similarity	NPC138472
0.8071	Intermediate Similarity	NPC180261
0.8071	Intermediate Similarity	NPC4170
0.8071	Intermediate Similarity	NPC139074
0.8071	Intermediate Similarity	NPC213485
0.8071	Intermediate Similarity	NPC40524
0.8071	Intermediate Similarity	NPC37299
0.8071	Intermediate Similarity	NPC111845
0.8069	Intermediate Similarity	NPC43158
0.8069	Intermediate Similarity	NPC472016
0.8069	Intermediate Similarity	NPC30846
0.8069	Intermediate Similarity	NPC469855
0.8069	Intermediate Similarity	NPC258469
0.8069	Intermediate Similarity	NPC192831
0.8069	Intermediate Similarity	NPC277315
0.8069	Intermediate Similarity	NPC471972
0.8069	Intermediate Similarity	NPC314271
0.8069	Intermediate Similarity	NPC471971
0.8067	Intermediate Similarity	NPC227485
0.8062	Intermediate Similarity	NPC114918
0.806	Intermediate Similarity	NPC86900
0.8058	Intermediate Similarity	NPC318799
0.8056	Intermediate Similarity	NPC3218
0.8056	Intermediate Similarity	NPC477279
0.8056	Intermediate Similarity	NPC470035
0.8054	Intermediate Similarity	NPC280753
0.8054	Intermediate Similarity	NPC306343
0.8054	Intermediate Similarity	NPC44378
0.8045	Intermediate Similarity	NPC165197
0.8043	Intermediate Similarity	NPC117899
0.8042	Intermediate Similarity	NPC61398
0.8042	Intermediate Similarity	NPC206207
0.8042	Intermediate Similarity	NPC416
0.8041	Intermediate Similarity	NPC43123
0.8041	Intermediate Similarity	NPC81835
0.8041	Intermediate Similarity	NPC127046
0.803	Intermediate Similarity	NPC476020
0.8029	Intermediate Similarity	NPC121104
0.8029	Intermediate Similarity	NPC324209
0.8029	Intermediate Similarity	NPC473787
0.8029	Intermediate Similarity	NPC107672
0.8028	Intermediate Similarity	NPC315275
0.8028	Intermediate Similarity	NPC156307
0.8028	Intermediate Similarity	NPC223836
0.8027	Intermediate Similarity	NPC470038
0.8027	Intermediate Similarity	NPC84786
0.8027	Intermediate Similarity	NPC83272
0.8026	Intermediate Similarity	NPC16082
0.8026	Intermediate Similarity	NPC180901
0.8026	Intermediate Similarity	NPC172920
0.8026	Intermediate Similarity	NPC156624
0.8026	Intermediate Similarity	NPC82592
0.8026	Intermediate Similarity	NPC300757
0.8015	Intermediate Similarity	NPC167055
0.8015	Intermediate Similarity	NPC160199
0.8015	Intermediate Similarity	NPC240744
0.8014	Intermediate Similarity	NPC474394
0.8014	Intermediate Similarity	NPC474692
0.8014	Intermediate Similarity	NPC106406
0.8014	Intermediate Similarity	NPC229036
0.8013	Intermediate Similarity	NPC323626
0.8013	Intermediate Similarity	NPC131121

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 NPC204582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	849
0.2-0.3	1793
0.3-0.4	2698
0.4-0.5	2001
0.5-0.6	1048
0.6-0.7	448
0.7-0.8	58
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD9269	Phase 2
0.8333	Intermediate Similarity	NPD230	Phase 1
0.803	Intermediate Similarity	NPD9268	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.7945	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD9545	Approved
0.7656	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD9494	Approved
0.763	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2935	Discontinued
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7517	Intermediate Similarity	NPD8166	Discontinued
0.745	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1934	Approved
0.7434	Intermediate Similarity	NPD2534	Approved
0.7434	Intermediate Similarity	NPD2533	Approved
0.7434	Intermediate Similarity	NPD2532	Approved
0.7432	Intermediate Similarity	NPD7266	Discontinued
0.7415	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6232	Discontinued
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7358	Intermediate Similarity	NPD7075	Discontinued
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7308	Intermediate Similarity	NPD4380	Phase 2
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2801	Approved
0.726	Intermediate Similarity	NPD825	Approved
0.726	Intermediate Similarity	NPD826	Approved
0.7254	Intermediate Similarity	NPD1164	Approved
0.7254	Intermediate Similarity	NPD1470	Approved
0.7251	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9570	Approved
0.7246	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD3455	Phase 2
0.7241	Intermediate Similarity	NPD3764	Approved
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7211	Intermediate Similarity	NPD447	Suspended
0.7203	Intermediate Similarity	NPD258	Approved
0.7203	Intermediate Similarity	NPD257	Approved
0.7195	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1465	Phase 2
0.717	Intermediate Similarity	NPD7819	Suspended
0.7169	Intermediate Similarity	NPD7054	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD7472	Approved
0.7125	Intermediate Similarity	NPD3817	Phase 2
0.7107	Intermediate Similarity	NPD6801	Discontinued
0.7101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1201	Approved
0.7068	Intermediate Similarity	NPD9266	Approved
0.7068	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD74	Approved
0.7067	Intermediate Similarity	NPD2799	Discontinued
0.7051	Intermediate Similarity	NPD1512	Approved
0.7044	Intermediate Similarity	NPD6386	Approved
0.7044	Intermediate Similarity	NPD6385	Approved
0.7041	Intermediate Similarity	NPD7251	Discontinued
0.7029	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD6234	Discontinued
0.6993	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9263	Approved
0.6992	Remote Similarity	NPD9267	Approved
0.6992	Remote Similarity	NPD9264	Approved
0.6987	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6797	Phase 2
0.698	Remote Similarity	NPD555	Phase 2
0.6971	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3300	Phase 2
0.6966	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD259	Phase 1
0.6959	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD1510	Phase 2
0.6951	Remote Similarity	NPD5494	Approved
0.695	Remote Similarity	NPD4626	Approved
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3400	Discontinued
0.6948	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3027	Phase 3
0.6937	Remote Similarity	NPD7411	Suspended
0.6933	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6799	Approved
0.6918	Remote Similarity	NPD3226	Approved
0.6918	Remote Similarity	NPD5736	Approved
0.6918	Remote Similarity	NPD9569	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6913	Remote Similarity	NPD1240	Approved
0.6909	Remote Similarity	NPD8127	Discontinued
0.6905	Remote Similarity	NPD7228	Approved
0.6901	Remote Similarity	NPD7808	Phase 3
0.6899	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2313	Discontinued
0.6884	Remote Similarity	NPD2629	Approved
0.6871	Remote Similarity	NPD4967	Phase 2
0.6871	Remote Similarity	NPD4966	Approved
0.6871	Remote Similarity	NPD4965	Approved
0.6871	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD275	Approved
0.6867	Remote Similarity	NPD274	Approved
0.6867	Remote Similarity	NPD6355	Discontinued
0.6864	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD6559	Discontinued
0.6839	Remote Similarity	NPD7003	Approved
0.6831	Remote Similarity	NPD9384	Approved
0.6831	Remote Similarity	NPD9381	Approved
0.6824	Remote Similarity	NPD9536	Phase 1
0.6824	Remote Similarity	NPD9537	Phase 1
0.6821	Remote Similarity	NPD1607	Approved
0.6818	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5402	Approved
0.681	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD919	Approved
0.6779	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6599	Discontinued
0.6769	Remote Similarity	NPD9495	Approved
0.6766	Remote Similarity	NPD5711	Approved
0.6766	Remote Similarity	NPD5710	Approved
0.6763	Remote Similarity	NPD8313	Approved
0.6763	Remote Similarity	NPD9281	Approved
0.6763	Remote Similarity	NPD8312	Approved
0.6761	Remote Similarity	NPD5691	Approved
0.6759	Remote Similarity	NPD9622	Approved
0.6753	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6004	Phase 3
0.6753	Remote Similarity	NPD6002	Phase 3
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6005	Phase 3
0.6753	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1653	Approved
0.6743	Remote Similarity	NPD8434	Phase 2
0.6732	Remote Similarity	NPD7033	Discontinued
0.6731	Remote Similarity	NPD3750	Approved
0.673	Remote Similarity	NPD6273	Approved
0.6715	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2932	Approved
0.6713	Remote Similarity	NPD3019	Approved
0.6712	Remote Similarity	NPD1283	Approved
0.6711	Remote Similarity	NPD6651	Approved
0.671	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD6959	Discontinued
0.6692	Remote Similarity	NPD9261	Approved
0.6691	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD9717	Approved
0.6689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1613	Approved
0.6688	Remote Similarity	NPD2796	Approved
0.6687	Remote Similarity	NPD920	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD228	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD7286	Phase 2
0.6646	Remote Similarity	NPD7236	Approved
0.6646	Remote Similarity	NPD8455	Phase 2
0.6645	Remote Similarity	NPD2344	Approved
0.6644	Remote Similarity	NPD6832	Phase 2
0.6643	Remote Similarity	NPD5951	Approved
0.6642	Remote Similarity	NPD1237	Approved
0.6627	Remote Similarity	NPD5242	Approved
0.6626	Remote Similarity	NPD6873	Phase 2
0.6625	Remote Similarity	NPD5049	Phase 3
0.6624	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD4308	Phase 3
0.6622	Remote Similarity	NPD9620	Approved
0.6622	Remote Similarity	NPD9619	Approved
0.6622	Remote Similarity	NPD9621	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