NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	334.553
LogP:	3.174
LogD:	2.321
LogS:	-4.631
# Rotatable Bonds:	0
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.005
Fsp3:	0.3
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:	-4.962
MDCK Permeability:	1.0622762601997238e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.291
20% Bioavailability (F20%):	0.48
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.46
Plasma Protein Binding (PPB):	90.68102264404297%
Volume Distribution (VD):	0.887
Pgp-substrate:	6.6566877365112305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.591
CYP1A2-substrate:	0.623
CYP2C19-inhibitor:	0.517
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	2.555
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.794
AMES Toxicity:	0.776
Rat Oral Acute Toxicity:	0.493
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.803
Carcinogencity:	0.814
Eye Corrosion:	0.003
Eye Irritation:	0.317
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC477275

Natural Product ID:	NPC477275
*Common Name:**	(2S,11S,12S)-2,7,17-trihydroxypentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),3(8),4,6,16,18-hexaene-9,15-dione
IUPAC Name:	(2S,11S,12S)-2,7,17-trihydroxypentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),3(8),4,6,16,18-hexaene-9,15-dione
Synonyms:	Daldinone C
Standard InCHIKey:	OYRYUFABCKQXTO-GWUBFIHGSA-N
Standard InCHI:	InChI=1S/C20H16O5/c21-13-3-1-2-10-18(13)16(24)8-12-9-4-6-14(22)19-15(23)7-5-11(17(9)19)20(10,12)25/h1-3,5,7,9,12,21,23,25H,4,6,8H2/t9-,12-,20+/m0/s1
SMILES:	C1CC(=O)C2=C(C=CC3=C2[C@@H]1[C@H]4[C@]3(C5=C(C(=O)C4)C(=CC=C5)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44418834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253861]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21082806]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148396]

☑ 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	=	49500	nM	PMID[17253861]

☑ 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 NPC477275 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	410
0.1-0.2	1624
0.2-0.3	3113
0.3-0.4	8935
0.4-0.5	10555
0.5-0.6	5470
0.6-0.7	8256
0.7-0.8	3987
0.8-0.85	286
0.85-0.9	55
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9172	High Similarity	NPC477276
0.8944	High Similarity	NPC85310
0.8936	High Similarity	NPC96421
0.8929	High Similarity	NPC13715
0.8873	High Similarity	NPC91019
0.8873	High Similarity	NPC106519
0.8811	High Similarity	NPC469520
0.8714	High Similarity	NPC283088
0.8714	High Similarity	NPC80035
0.8696	High Similarity	NPC474517
0.8696	High Similarity	NPC72669
0.8686	High Similarity	NPC99731
0.8681	High Similarity	NPC257644
0.8681	High Similarity	NPC239136
0.8681	High Similarity	NPC19631
0.8671	High Similarity	NPC169452
0.8671	High Similarity	NPC181560
0.8662	High Similarity	NPC20210
0.8643	High Similarity	NPC161964
0.8643	High Similarity	NPC287604
0.8643	High Similarity	NPC472262
0.8621	High Similarity	NPC313047
0.8621	High Similarity	NPC474203
0.8621	High Similarity	NPC471682
0.8621	High Similarity	NPC296752
0.8621	High Similarity	NPC295712
0.8621	High Similarity	NPC451542
0.8601	High Similarity	NPC138099
0.8601	High Similarity	NPC242994
0.8592	High Similarity	NPC245923
0.8571	High Similarity	NPC225051
0.8571	High Similarity	NPC115458
0.8571	High Similarity	NPC52407
0.8552	High Similarity	NPC193555
0.8542	High Similarity	NPC225243
0.8529	High Similarity	NPC103540
0.8521	High Similarity	NPC474813
0.8521	High Similarity	NPC272268
0.8521	High Similarity	NPC191976
0.8521	High Similarity	NPC155211
0.8514	High Similarity	NPC52161
0.8514	High Similarity	NPC162751
0.8511	High Similarity	NPC166480
0.8511	High Similarity	NPC44437
0.8511	High Similarity	NPC282780
0.8511	High Similarity	NPC50924
0.8503	High Similarity	NPC471683
0.85	High Similarity	NPC70622
0.85	High Similarity	NPC58685
0.8493	Intermediate Similarity	NPC174905
0.8493	Intermediate Similarity	NPC293545
0.8489	Intermediate Similarity	NPC108129
0.8483	Intermediate Similarity	NPC246638
0.8478	Intermediate Similarity	NPC48248
0.8478	Intermediate Similarity	NPC282923
0.8467	Intermediate Similarity	NPC315520
0.8462	Intermediate Similarity	NPC471905
0.8462	Intermediate Similarity	NPC53206
0.8462	Intermediate Similarity	NPC53414
0.8456	Intermediate Similarity	NPC290695
0.8456	Intermediate Similarity	NPC173978
0.8456	Intermediate Similarity	NPC106524
0.8456	Intermediate Similarity	NPC142846
0.8451	Intermediate Similarity	NPC477596
0.8446	Intermediate Similarity	NPC147250
0.844	Intermediate Similarity	NPC314048
0.844	Intermediate Similarity	NPC267205
0.8435	Intermediate Similarity	NPC227841
0.8435	Intermediate Similarity	NPC10764
0.8429	Intermediate Similarity	NPC244699
0.8429	Intermediate Similarity	NPC205992
0.8425	Intermediate Similarity	NPC474961
0.8417	Intermediate Similarity	NPC276238
0.8403	Intermediate Similarity	NPC416
0.8403	Intermediate Similarity	NPC61398
0.8392	Intermediate Similarity	NPC254847
0.8392	Intermediate Similarity	NPC193358
0.8389	Intermediate Similarity	NPC37709
0.8389	Intermediate Similarity	NPC215593
0.8389	Intermediate Similarity	NPC472135
0.8389	Intermediate Similarity	NPC119767
0.8382	Intermediate Similarity	NPC375356
0.838	Intermediate Similarity	NPC288089
0.838	Intermediate Similarity	NPC477594
0.838	Intermediate Similarity	NPC202225
0.8369	Intermediate Similarity	NPC175738
0.8357	Intermediate Similarity	NPC136588
0.8357	Intermediate Similarity	NPC199253
0.8345	Intermediate Similarity	NPC143438
0.8345	Intermediate Similarity	NPC96024
0.8345	Intermediate Similarity	NPC190457
0.8333	Intermediate Similarity	NPC474110
0.8333	Intermediate Similarity	NPC3224
0.8333	Intermediate Similarity	NPC62272
0.8333	Intermediate Similarity	NPC96915
0.8333	Intermediate Similarity	NPC147418
0.8333	Intermediate Similarity	NPC44960
0.8333	Intermediate Similarity	NPC53001
0.8322	Intermediate Similarity	NPC271944
0.8322	Intermediate Similarity	NPC110882
0.8322	Intermediate Similarity	NPC285122
0.8322	Intermediate Similarity	NPC85393
0.8322	Intermediate Similarity	NPC472134
0.8321	Intermediate Similarity	NPC199273
0.8311	Intermediate Similarity	NPC300684
0.8311	Intermediate Similarity	NPC218866
0.8311	Intermediate Similarity	NPC84568
0.8311	Intermediate Similarity	NPC48130
0.831	Intermediate Similarity	NPC294226
0.831	Intermediate Similarity	NPC53896
0.8309	Intermediate Similarity	NPC91478
0.8309	Intermediate Similarity	NPC300274
0.8301	Intermediate Similarity	NPC218870
0.8301	Intermediate Similarity	NPC474824
0.8301	Intermediate Similarity	NPC470408
0.8301	Intermediate Similarity	NPC182921
0.8299	Intermediate Similarity	NPC137649
0.8299	Intermediate Similarity	NPC135524
0.8298	Intermediate Similarity	NPC41847
0.8296	Intermediate Similarity	NPC190971
0.8288	Intermediate Similarity	NPC315578
0.8286	Intermediate Similarity	NPC34414
0.8286	Intermediate Similarity	NPC92624
0.8286	Intermediate Similarity	NPC146647
0.8278	Intermediate Similarity	NPC477221
0.8278	Intermediate Similarity	NPC478219
0.8276	Intermediate Similarity	NPC4214
0.8276	Intermediate Similarity	NPC87723
0.8273	Intermediate Similarity	NPC176130
0.8273	Intermediate Similarity	NPC78364
0.8273	Intermediate Similarity	NPC84672
0.8273	Intermediate Similarity	NPC69424
0.8267	Intermediate Similarity	NPC290194
0.8264	Intermediate Similarity	NPC118919
0.8255	Intermediate Similarity	NPC170055
0.8255	Intermediate Similarity	NPC12402
0.8252	Intermediate Similarity	NPC12070
0.8235	Intermediate Similarity	NPC120545
0.8231	Intermediate Similarity	NPC290550
0.8231	Intermediate Similarity	NPC204045
0.8231	Intermediate Similarity	NPC305845
0.8227	Intermediate Similarity	NPC259942
0.8227	Intermediate Similarity	NPC55949
0.8224	Intermediate Similarity	NPC205766
0.8219	Intermediate Similarity	NPC26924
0.8207	Intermediate Similarity	NPC477592
0.8207	Intermediate Similarity	NPC305060
0.82	Intermediate Similarity	NPC143685
0.82	Intermediate Similarity	NPC314437
0.8194	Intermediate Similarity	NPC258502
0.8194	Intermediate Similarity	NPC474861
0.8194	Intermediate Similarity	NPC249272
0.8188	Intermediate Similarity	NPC471906
0.8188	Intermediate Similarity	NPC142956
0.8188	Intermediate Similarity	NPC244691
0.8188	Intermediate Similarity	NPC193703
0.8188	Intermediate Similarity	NPC79627
0.8188	Intermediate Similarity	NPC21599
0.8182	Intermediate Similarity	NPC114183
0.8176	Intermediate Similarity	NPC477209
0.8176	Intermediate Similarity	NPC73061
0.8169	Intermediate Similarity	NPC93015
0.8169	Intermediate Similarity	NPC85342
0.8169	Intermediate Similarity	NPC471851
0.8163	Intermediate Similarity	NPC203063
0.8158	Intermediate Similarity	NPC329933
0.8156	Intermediate Similarity	NPC474998
0.8156	Intermediate Similarity	NPC303910
0.8151	Intermediate Similarity	NPC477593
0.8146	Intermediate Similarity	NPC478018
0.8143	Intermediate Similarity	NPC471530
0.8143	Intermediate Similarity	NPC72667
0.8138	Intermediate Similarity	NPC472308
0.8133	Intermediate Similarity	NPC68441
0.8133	Intermediate Similarity	NPC34482
0.8133	Intermediate Similarity	NPC478019
0.8129	Intermediate Similarity	NPC66029
0.8125	Intermediate Similarity	NPC270899
0.8125	Intermediate Similarity	NPC52368
0.8125	Intermediate Similarity	NPC218854
0.8121	Intermediate Similarity	NPC238629
0.8121	Intermediate Similarity	NPC53016
0.8108	Intermediate Similarity	NPC187843
0.8099	Intermediate Similarity	NPC31799
0.8085	Intermediate Similarity	NPC21305
0.8085	Intermediate Similarity	NPC473017
0.8085	Intermediate Similarity	NPC247250
0.8085	Intermediate Similarity	NPC767
0.8082	Intermediate Similarity	NPC36868
0.8082	Intermediate Similarity	NPC49911
0.8082	Intermediate Similarity	NPC277559
0.8079	Intermediate Similarity	NPC477208
0.8079	Intermediate Similarity	NPC470570
0.8077	Intermediate Similarity	NPC478223
0.8071	Intermediate Similarity	NPC267846
0.8071	Intermediate Similarity	NPC254492
0.8071	Intermediate Similarity	NPC231774
0.8071	Intermediate Similarity	NPC8745
0.8071	Intermediate Similarity	NPC306765
0.8071	Intermediate Similarity	NPC160499

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 NPC477275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	937
0.2-0.3	1421
0.3-0.4	2736
0.4-0.5	2151
0.5-0.6	1076
0.6-0.7	391
0.7-0.8	56
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD1470	Approved
0.8507	High Similarity	NPD1201	Approved
0.8435	Intermediate Similarity	NPD7390	Discontinued
0.8392	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5406	Approved
0.8333	Intermediate Similarity	NPD5405	Approved
0.8333	Intermediate Similarity	NPD5408	Approved
0.8333	Intermediate Similarity	NPD5404	Approved
0.8133	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD3019	Approved
0.7881	Intermediate Similarity	NPD3300	Phase 2
0.7826	Intermediate Similarity	NPD2932	Approved
0.774	Intermediate Similarity	NPD943	Approved
0.7664	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3764	Approved
0.758	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.7546	Intermediate Similarity	NPD6959	Discontinued
0.7533	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3023	Approved
0.7518	Intermediate Similarity	NPD3026	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD3025	Approved
0.75	Intermediate Similarity	NPD3024	Approved
0.7447	Intermediate Similarity	NPD4059	Approved
0.7436	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7432	Intermediate Similarity	NPD6663	Approved
0.7397	Intermediate Similarity	NPD5736	Approved
0.7389	Intermediate Similarity	NPD6273	Approved
0.7379	Intermediate Similarity	NPD1164	Approved
0.7368	Intermediate Similarity	NPD2935	Discontinued
0.7362	Intermediate Similarity	NPD3749	Approved
0.7346	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2533	Approved
0.7325	Intermediate Similarity	NPD2532	Approved
0.7325	Intermediate Similarity	NPD2534	Approved
0.7312	Intermediate Similarity	NPD4380	Phase 2
0.7305	Intermediate Similarity	NPD3091	Approved
0.7303	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD1510	Phase 2
0.729	Intermediate Similarity	NPD7003	Approved
0.7284	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7819	Suspended
0.726	Intermediate Similarity	NPD3094	Phase 2
0.7254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3092	Approved
0.7208	Intermediate Similarity	NPD2344	Approved
0.7171	Intermediate Similarity	NPD1607	Approved
0.7161	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7133	Intermediate Similarity	NPD2313	Discontinued
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2798	Approved
0.7089	Intermediate Similarity	NPD7236	Approved
0.7083	Intermediate Similarity	NPD3095	Discontinued
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1876	Approved
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD2801	Approved
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.707	Intermediate Similarity	NPD3750	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7066	Intermediate Similarity	NPD5494	Approved
0.7063	Intermediate Similarity	NPD1512	Approved
0.7062	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7411	Suspended
0.7051	Intermediate Similarity	NPD1549	Phase 2
0.7025	Intermediate Similarity	NPD2309	Approved
0.7012	Intermediate Similarity	NPD1934	Approved
0.7007	Intermediate Similarity	NPD2342	Discontinued
0.7006	Intermediate Similarity	NPD2800	Approved
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7635	Approved
0.6993	Remote Similarity	NPD7610	Discontinued
0.6988	Remote Similarity	NPD7768	Phase 2
0.6962	Remote Similarity	NPD8166	Discontinued
0.6954	Remote Similarity	NPD5031	Approved
0.6954	Remote Similarity	NPD5029	Approved
0.6954	Remote Similarity	NPD5027	Approved
0.6939	Remote Similarity	NPD4878	Approved
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6534	Approved
0.6906	Remote Similarity	NPD6535	Approved
0.6901	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6166	Phase 2
0.6901	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5951	Approved
0.6894	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7028	Phase 2
0.6886	Remote Similarity	NPD3882	Suspended
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1471	Phase 3
0.6879	Remote Similarity	NPD5844	Phase 1
0.6879	Remote Similarity	NPD6020	Phase 2
0.6871	Remote Similarity	NPD7239	Suspended
0.6867	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4624	Approved
0.6846	Remote Similarity	NPD1283	Approved
0.6845	Remote Similarity	NPD7075	Discontinued
0.6845	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3818	Discontinued
0.6818	Remote Similarity	NPD5026	Approved
0.6818	Remote Similarity	NPD5028	Approved
0.6818	Remote Similarity	NPD4954	Approved
0.6818	Remote Similarity	NPD4955	Approved
0.6818	Remote Similarity	NPD36	Approved
0.6818	Remote Similarity	NPD5034	Approved
0.6815	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD2796	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6811	Remote Similarity	NPD6782	Approved
0.6811	Remote Similarity	NPD6777	Approved
0.6811	Remote Similarity	NPD6776	Approved
0.6811	Remote Similarity	NPD6779	Approved
0.6811	Remote Similarity	NPD6781	Approved
0.6811	Remote Similarity	NPD6778	Approved
0.6811	Remote Similarity	NPD6780	Approved
0.6793	Remote Similarity	NPD7700	Phase 2
0.6793	Remote Similarity	NPD7699	Phase 2
0.6786	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5711	Approved
0.6784	Remote Similarity	NPD5710	Approved
0.6781	Remote Similarity	NPD1651	Approved
0.6778	Remote Similarity	NPD6836	Approved
0.6766	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7685	Pre-registration
0.6761	Remote Similarity	NPD5030	Phase 2
0.676	Remote Similarity	NPD5037	Approved
0.676	Remote Similarity	NPD5038	Approved
0.6755	Remote Similarity	NPD8320	Phase 1
0.6755	Remote Similarity	NPD8319	Approved
0.6753	Remote Similarity	NPD8032	Phase 2
0.6752	Remote Similarity	NPD3748	Approved
0.6741	Remote Similarity	NPD3020	Approved
0.6735	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6651	Approved
0.6725	Remote Similarity	NPD8127	Discontinued
0.6724	Remote Similarity	NPD7177	Discontinued
0.6714	Remote Similarity	NPD74	Approved
0.6714	Remote Similarity	NPD9266	Approved
0.6712	Remote Similarity	NPD7009	Phase 2
0.6711	Remote Similarity	NPD3972	Approved
0.6711	Remote Similarity	NPD2861	Phase 2
0.6711	Remote Similarity	NPD9269	Phase 2
0.6708	Remote Similarity	NPD6190	Approved
0.6704	Remote Similarity	NPD5036	Approved
0.6703	Remote Similarity	NPD5968	Phase 3
0.6702	Remote Similarity	NPD7697	Approved
0.6702	Remote Similarity	NPD7698	Approved
0.6702	Remote Similarity	NPD7435	Discontinued
0.6702	Remote Similarity	NPD7696	Phase 3
0.6689	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD5033	Approved
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7871	Phase 2
0.6667	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6667	Remote Similarity	NPD3022	Approved
0.6648	Remote Similarity	NPD7074	Phase 3
0.6646	Remote Similarity	NPD3400	Discontinued
0.6646	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD7961	Discontinued
0.6644	Remote Similarity	NPD1281	Approved
0.6643	Remote Similarity	NPD9264	Approved
0.6643	Remote Similarity	NPD9267	Approved
0.6643	Remote Similarity	NPD9263	Approved
0.6629	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7799	Discontinued
0.6629	Remote Similarity	NPD5032	Approved
0.6627	Remote Similarity	NPD3817	Phase 2
0.6626	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4626	Approved
0.6622	Remote Similarity	NPD2286	Discontinued
0.6622	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD37	Approved
0.6607	Remote Similarity	NPD6801	Discontinued
0.6603	Remote Similarity	NPD2979	Phase 3
0.6603	Remote Similarity	NPD4140	Approved
0.66	Remote Similarity	NPD1608	Approved
0.6599	Remote Similarity	NPD9545	Approved
0.6592	Remote Similarity	NPD5035	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