NPASS Compound

Structure

CID183781 OpenBabel06191715562D 25 29 0 0 1 0 0 0 0 0999 V2000 2.4780 -4.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8474 -0.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3036 -2.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1997 -0.6141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3035 -1.9065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2217 -0.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6513 0.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8257 1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6522 -2.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5610 1.0798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4777 -3.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8694 0.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4777 -1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9134 0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6518 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5830 1.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1054 1.9476 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8258 -0.4768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6517 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0001 0.9532 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6373 2.6173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 0.5004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0837 2.1548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8262 -1.4304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 22 1 6 0 0 0 20 8 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	339.826
LogP:	3.469
LogD:	3.192
LogS:	-4.984
# Rotatable Bonds:	0
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	4.709
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.731
MDCK Permeability:	1.9399254597374238e-05
Pgp-inhibitor:	0.4
Pgp-substrate:	0.206
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.488
Plasma Protein Binding (PPB):	94.62164306640625%
Volume Distribution (VD):	0.817
Pgp-substrate:	3.1265883445739746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.216
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.513
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.836

ADMET: Excretion

Clearance (CL):	4.194
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.293
AMES Toxicity:	0.975
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.345
Carcinogencity:	0.978
Eye Corrosion:	0.003
Eye Irritation:	0.11
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC183781

Natural Product ID:	NPC183781
*Common Name:**	3',4',4A',9A'-Tetrahydro-6,7'-Dimethylspiro[Benzofuran-3(2H),2'-Pyrano[2,3-B]Benzofuran]-2,4A'-Diol
IUPAC Name:	(2S,3S,4'aR,9'aS)-6,7'-dimethylspiro[2H-1-benzofuran-3,2'-4,9a-dihydro-3H-pyrano[2,3-b][1]benzofuran]-2,4'a-diol
Synonyms:
Standard InCHIKey:	YMKQULZUUJUBPP-HAGHYFMRSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-11-3-5-13-15(9-11)24-18-19(13,22)7-8-20(25-18)14-6-4-12(2)10-16(14)23-17(20)21/h3-6,9-10,17-18,21-22H,7-8H2,1-2H3/t17-,18-,19+,20-/m0/s1
SMILES:	Cc1ccc2c(c1)O[C@@H]1[C@]2(CC[C@@]2(c3ccc(C)cc3O[C@@H]2O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486806
PubChem CID:	44559245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974630]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	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	2

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	12000.0	nM	PMID[510615]
NPT2	Others	Unspecified		IC50	=	4200.0	nM	PMID[510615]

☑ 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 NPC183781 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	370
0.1-0.2	1427
0.2-0.3	3363
0.3-0.4	9146
0.4-0.5	9680
0.5-0.6	4757
0.6-0.7	9839
0.7-0.8	3653
0.8-0.85	391
0.85-0.9	68
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9191	High Similarity	NPC134260
0.8993	High Similarity	NPC210192
0.8873	High Similarity	NPC18979
0.8828	High Similarity	NPC98624
0.8811	High Similarity	NPC162193
0.8811	High Similarity	NPC112861
0.8794	High Similarity	NPC246947
0.8794	High Similarity	NPC472353
0.875	High Similarity	NPC475067
0.8741	High Similarity	NPC38041
0.8741	High Similarity	NPC476301
0.8741	High Similarity	NPC97326
0.8741	High Similarity	NPC469586
0.8741	High Similarity	NPC43508
0.8741	High Similarity	NPC22150
0.8741	High Similarity	NPC279298
0.8732	High Similarity	NPC46092
0.8723	High Similarity	NPC108674
0.8722	High Similarity	NPC470510
0.8707	High Similarity	NPC474442
0.8671	High Similarity	NPC283995
0.8671	High Similarity	NPC79429
0.8671	High Similarity	NPC84181
0.8671	High Similarity	NPC129417
0.8671	High Similarity	NPC471667
0.8671	High Similarity	NPC470235
0.8671	High Similarity	NPC217635
0.8633	High Similarity	NPC79957
0.863	High Similarity	NPC55158
0.863	High Similarity	NPC286235
0.863	High Similarity	NPC51328
0.8623	High Similarity	NPC215037
0.8621	High Similarity	NPC275284
0.8621	High Similarity	NPC114505
0.8621	High Similarity	NPC193473
0.8621	High Similarity	NPC15956
0.8621	High Similarity	NPC224674
0.8621	High Similarity	NPC31325
0.8621	High Similarity	NPC213074
0.8603	High Similarity	NPC218003
0.8601	High Similarity	NPC477898
0.8601	High Similarity	NPC81638
0.8601	High Similarity	NPC185307
0.8601	High Similarity	NPC470950
0.8582	High Similarity	NPC156376
0.8571	High Similarity	NPC475224
0.8571	High Similarity	NPC3049
0.8571	High Similarity	NPC238140
0.8571	High Similarity	NPC469383
0.8571	High Similarity	NPC475628
0.8562	High Similarity	NPC166584
0.8562	High Similarity	NPC270751
0.8562	High Similarity	NPC248132
0.8562	High Similarity	NPC130449
0.8562	High Similarity	NPC301961
0.8561	High Similarity	NPC226712
0.8561	High Similarity	NPC211164
0.8552	High Similarity	NPC276753
0.8552	High Similarity	NPC205796
0.8552	High Similarity	NPC190714
0.8552	High Similarity	NPC99515
0.854	High Similarity	NPC262606
0.8531	High Similarity	NPC476356
0.8531	High Similarity	NPC302506
0.8531	High Similarity	NPC253878
0.8531	High Similarity	NPC174522
0.8529	High Similarity	NPC40377
0.8521	High Similarity	NPC226547
0.8511	High Similarity	NPC262328
0.8511	High Similarity	NPC87777
0.8511	High Similarity	NPC185908
0.8511	High Similarity	NPC474687
0.85	High Similarity	NPC174191
0.8496	Intermediate Similarity	NPC188997
0.8493	Intermediate Similarity	NPC39657
0.8489	Intermediate Similarity	NPC25821
0.8489	Intermediate Similarity	NPC115022
0.8489	Intermediate Similarity	NPC294166
0.8483	Intermediate Similarity	NPC475096
0.8483	Intermediate Similarity	NPC178014
0.8483	Intermediate Similarity	NPC307466
0.8483	Intermediate Similarity	NPC180953
0.8483	Intermediate Similarity	NPC11422
0.8483	Intermediate Similarity	NPC474749
0.8483	Intermediate Similarity	NPC42716
0.8478	Intermediate Similarity	NPC162801
0.8478	Intermediate Similarity	NPC121376
0.8472	Intermediate Similarity	NPC473044
0.8467	Intermediate Similarity	NPC159922
0.8462	Intermediate Similarity	NPC471414
0.8462	Intermediate Similarity	NPC472711
0.8462	Intermediate Similarity	NPC471908
0.8462	Intermediate Similarity	NPC5155
0.8456	Intermediate Similarity	NPC469386
0.8451	Intermediate Similarity	NPC292487
0.8446	Intermediate Similarity	NPC472709
0.8446	Intermediate Similarity	NPC472710
0.844	Intermediate Similarity	NPC126101
0.844	Intermediate Similarity	NPC172818
0.844	Intermediate Similarity	NPC25695
0.844	Intermediate Similarity	NPC327735
0.8435	Intermediate Similarity	NPC175976
0.8435	Intermediate Similarity	NPC71726
0.8433	Intermediate Similarity	NPC261992
0.8429	Intermediate Similarity	NPC87696
0.8429	Intermediate Similarity	NPC187194
0.8429	Intermediate Similarity	NPC117048
0.8429	Intermediate Similarity	NPC124085
0.8429	Intermediate Similarity	NPC476411
0.8425	Intermediate Similarity	NPC226540
0.8425	Intermediate Similarity	NPC125755
0.8417	Intermediate Similarity	NPC259742
0.8417	Intermediate Similarity	NPC219671
0.8417	Intermediate Similarity	NPC85799
0.8417	Intermediate Similarity	NPC165686
0.8417	Intermediate Similarity	NPC26080
0.8417	Intermediate Similarity	NPC104077
0.8417	Intermediate Similarity	NPC7744
0.8417	Intermediate Similarity	NPC303422
0.8417	Intermediate Similarity	NPC147616
0.8414	Intermediate Similarity	NPC471063
0.8414	Intermediate Similarity	NPC168579
0.8414	Intermediate Similarity	NPC138227
0.8414	Intermediate Similarity	NPC76176
0.8414	Intermediate Similarity	NPC473045
0.8414	Intermediate Similarity	NPC25292
0.8414	Intermediate Similarity	NPC469313
0.8414	Intermediate Similarity	NPC179521
0.8406	Intermediate Similarity	NPC474491
0.8406	Intermediate Similarity	NPC325003
0.8403	Intermediate Similarity	NPC475084
0.8403	Intermediate Similarity	NPC60249
0.8403	Intermediate Similarity	NPC80326
0.8403	Intermediate Similarity	NPC189115
0.84	Intermediate Similarity	NPC78809
0.838	Intermediate Similarity	NPC283949
0.838	Intermediate Similarity	NPC470413
0.838	Intermediate Similarity	NPC138738
0.8378	Intermediate Similarity	NPC44452
0.8378	Intermediate Similarity	NPC95392
0.8378	Intermediate Similarity	NPC55715
0.8378	Intermediate Similarity	NPC35877
0.8378	Intermediate Similarity	NPC240521
0.837	Intermediate Similarity	NPC287429
0.8369	Intermediate Similarity	NPC184938
0.8369	Intermediate Similarity	NPC238243
0.8369	Intermediate Similarity	NPC101624
0.8369	Intermediate Similarity	NPC18576
0.8369	Intermediate Similarity	NPC142547
0.8369	Intermediate Similarity	NPC135777
0.8367	Intermediate Similarity	NPC227902
0.8367	Intermediate Similarity	NPC15538
0.8367	Intermediate Similarity	NPC473480
0.8357	Intermediate Similarity	NPC85435
0.8357	Intermediate Similarity	NPC169973
0.8356	Intermediate Similarity	NPC161700
0.8356	Intermediate Similarity	NPC277867
0.8355	Intermediate Similarity	NPC189730
0.8345	Intermediate Similarity	NPC265154
0.8345	Intermediate Similarity	NPC474808
0.8345	Intermediate Similarity	NPC472590
0.8345	Intermediate Similarity	NPC166168
0.8345	Intermediate Similarity	NPC37793
0.8333	Intermediate Similarity	NPC472797
0.8333	Intermediate Similarity	NPC302610
0.8333	Intermediate Similarity	NPC21902
0.8333	Intermediate Similarity	NPC233467
0.8333	Intermediate Similarity	NPC58137
0.8333	Intermediate Similarity	NPC26653
0.8333	Intermediate Similarity	NPC300798
0.8333	Intermediate Similarity	NPC76871
0.8333	Intermediate Similarity	NPC469661
0.8333	Intermediate Similarity	NPC270849
0.8333	Intermediate Similarity	NPC59692
0.8322	Intermediate Similarity	NPC88640
0.8322	Intermediate Similarity	NPC193666
0.8322	Intermediate Similarity	NPC123526
0.8322	Intermediate Similarity	NPC475836
0.831	Intermediate Similarity	NPC18189
0.831	Intermediate Similarity	NPC52277
0.831	Intermediate Similarity	NPC199459
0.831	Intermediate Similarity	NPC262585
0.831	Intermediate Similarity	NPC104167
0.831	Intermediate Similarity	NPC40664
0.831	Intermediate Similarity	NPC472800
0.831	Intermediate Similarity	NPC177035
0.831	Intermediate Similarity	NPC165482
0.831	Intermediate Similarity	NPC197723
0.831	Intermediate Similarity	NPC138350
0.831	Intermediate Similarity	NPC3293
0.831	Intermediate Similarity	NPC20829
0.8309	Intermediate Similarity	NPC12308
0.8299	Intermediate Similarity	NPC241846
0.8299	Intermediate Similarity	NPC93610
0.8298	Intermediate Similarity	NPC470881
0.8298	Intermediate Similarity	NPC90083
0.8298	Intermediate Similarity	NPC188555
0.8298	Intermediate Similarity	NPC478085
0.8298	Intermediate Similarity	NPC170779
0.8298	Intermediate Similarity	NPC130496

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 NPC183781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	821
0.2-0.3	1599
0.3-0.4	2764
0.4-0.5	1842
0.5-0.6	1096
0.6-0.7	634
0.7-0.8	88
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD1091	Approved
0.8082	Intermediate Similarity	NPD6674	Discontinued
0.8071	Intermediate Similarity	NPD4625	Phase 3
0.8029	Intermediate Similarity	NPD4749	Approved
0.8028	Intermediate Similarity	NPD1613	Approved
0.8028	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2861	Phase 2
0.7919	Intermediate Similarity	NPD5058	Phase 3
0.7872	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7868	Intermediate Similarity	NPD5125	Phase 3
0.7868	Intermediate Similarity	NPD5126	Approved
0.7801	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4967	Phase 2
0.7771	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD4965	Approved
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1610	Phase 2
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7673	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD7228	Approved
0.763	Intermediate Similarity	NPD6671	Approved
0.7626	Intermediate Similarity	NPD3705	Approved
0.7589	Intermediate Similarity	NPD6696	Suspended
0.7584	Intermediate Similarity	NPD5763	Approved
0.7584	Intermediate Similarity	NPD5762	Approved
0.758	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD1653	Approved
0.7534	Intermediate Similarity	NPD4060	Phase 1
0.7532	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7266	Discontinued
0.7465	Intermediate Similarity	NPD8651	Approved
0.7464	Intermediate Similarity	NPD1548	Phase 1
0.7455	Intermediate Similarity	NPD3818	Discontinued
0.745	Intermediate Similarity	NPD7033	Discontinued
0.745	Intermediate Similarity	NPD5588	Approved
0.7424	Intermediate Similarity	NPD290	Approved
0.7403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6100	Approved
0.74	Intermediate Similarity	NPD6099	Approved
0.7383	Intermediate Similarity	NPD4538	Approved
0.7383	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4536	Approved
0.7381	Intermediate Similarity	NPD7240	Approved
0.7372	Intermediate Similarity	NPD7157	Approved
0.7368	Intermediate Similarity	NPD2684	Approved
0.7365	Intermediate Similarity	NPD7074	Phase 3
0.7365	Intermediate Similarity	NPD5735	Approved
0.7329	Intermediate Similarity	NPD7095	Approved
0.732	Intermediate Similarity	NPD4628	Phase 3
0.732	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3787	Discontinued
0.7305	Intermediate Similarity	NPD7054	Approved
0.7294	Intermediate Similarity	NPD8312	Approved
0.7294	Intermediate Similarity	NPD8313	Approved
0.7286	Intermediate Similarity	NPD1357	Approved
0.7279	Intermediate Similarity	NPD7843	Approved
0.7262	Intermediate Similarity	NPD7472	Approved
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.7237	Intermediate Similarity	NPD6002	Phase 3
0.7237	Intermediate Similarity	NPD6005	Phase 3
0.7237	Intermediate Similarity	NPD6004	Phase 3
0.7237	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1778	Approved
0.7219	Intermediate Similarity	NPD5960	Phase 3
0.7219	Intermediate Similarity	NPD4108	Discontinued
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7208	Intermediate Similarity	NPD3892	Phase 2
0.7202	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6653	Approved
0.719	Intermediate Similarity	NPD2424	Discontinued
0.7183	Intermediate Similarity	NPD3496	Discontinued
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7172	Intermediate Similarity	NPD2797	Approved
0.7162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.7161	Intermediate Similarity	NPD2677	Approved
0.7152	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7133	Intermediate Similarity	NPD1611	Approved
0.7124	Intermediate Similarity	NPD1375	Discontinued
0.7113	Intermediate Similarity	NPD6516	Phase 2
0.7113	Intermediate Similarity	NPD5846	Approved
0.7102	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5283	Phase 1
0.7101	Intermediate Similarity	NPD1398	Phase 1
0.7101	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5929	Approved
0.709	Intermediate Similarity	NPD968	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7071	Intermediate Similarity	NPD7340	Approved
0.7067	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD2238	Phase 2
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6032	Approved
0.7047	Intermediate Similarity	NPD3268	Approved
0.7047	Intermediate Similarity	NPD7985	Registered
0.7035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5177	Phase 3
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD4626	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6987	Remote Similarity	NPD7466	Approved
0.6986	Remote Similarity	NPD3225	Approved
0.6975	Remote Similarity	NPD6072	Discontinued
0.6974	Remote Similarity	NPD6353	Approved
0.6974	Remote Similarity	NPD4097	Suspended
0.6966	Remote Similarity	NPD2235	Phase 2
0.6966	Remote Similarity	NPD2232	Approved
0.6966	Remote Similarity	NPD2230	Approved
0.6966	Remote Similarity	NPD2233	Approved
0.6966	Remote Similarity	NPD2231	Phase 2
0.6959	Remote Similarity	NPD3018	Phase 2
0.6954	Remote Similarity	NPD3620	Phase 2
0.6954	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5402	Approved
0.6934	Remote Similarity	NPD4750	Phase 3
0.6933	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5585	Approved
0.6923	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5327	Phase 3
0.6918	Remote Similarity	NPD7447	Phase 1
0.6918	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4380	Phase 2
0.6914	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD3882	Suspended
0.6908	Remote Similarity	NPD4340	Discontinued
0.6906	Remote Similarity	NPD5535	Approved
0.6903	Remote Similarity	NPD2346	Discontinued
0.6899	Remote Similarity	NPD3122	Phase 3
0.6897	Remote Similarity	NPD422	Phase 1
0.689	Remote Similarity	NPD7819	Suspended
0.689	Remote Similarity	NPD2977	Approved
0.689	Remote Similarity	NPD2801	Approved
0.689	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2978	Approved
0.6886	Remote Similarity	NPD4666	Phase 3
0.6883	Remote Similarity	NPD2154	Approved
0.6883	Remote Similarity	NPD2156	Approved
0.6883	Remote Similarity	NPD2155	Approved
0.6879	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD4535	Phase 3
0.6879	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD17	Approved
0.6868	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7075	Discontinued
0.6867	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2970	Approved
0.6864	Remote Similarity	NPD2969	Approved
0.6857	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7212	Phase 2
0.6855	Remote Similarity	NPD7213	Phase 3
0.6852	Remote Similarity	NPD3226	Approved
0.6852	Remote Similarity	NPD7458	Discontinued
0.6848	Remote Similarity	NPD3817	Phase 2
0.6846	Remote Similarity	NPD1712	Approved
0.6842	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1551	Phase 2
0.6835	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD228	Approved
0.6832	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5403	Approved
0.6831	Remote Similarity	NPD6776	Approved
0.6831	Remote Similarity	NPD6781	Approved
0.6831	Remote Similarity	NPD6778	Approved
0.6831	Remote Similarity	NPD6782	Approved
0.6831	Remote Similarity	NPD6777	Approved
0.6831	Remote Similarity	NPD6780	Approved
0.6831	Remote Similarity	NPD6779	Approved
0.6829	Remote Similarity	NPD3382	Approved
0.6829	Remote Similarity	NPD3383	Approved
0.6829	Remote Similarity	NPD3384	Approved
0.6826	Remote Similarity	NPD5709	Phase 3
0.6824	Remote Similarity	NPD3094	Phase 2
0.6815	Remote Similarity	NPD5061	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