NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	352.13
Volume:	354.486
LogP:	2.926
LogD:	2.576
LogS:	-4.251
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	4.322
Fsp3:	0.381
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:	-4.9
MDCK Permeability:	1.0046684110420756e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.34
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.648
Plasma Protein Binding (PPB):	86.84772491455078%
Volume Distribution (VD):	1.069
Pgp-substrate:	8.899227142333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.644
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.355
CYP2D6-substrate:	0.32
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	4.94
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.284
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.609
AMES Toxicity:	0.81
Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.944
Carcinogencity:	0.77
Eye Corrosion:	0.003
Eye Irritation:	0.246
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC477276

Natural Product ID:	NPC477276
*Common Name:**	(2S,9S,11S,12S)-2,7,17-trihydroxy-9-methoxypentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),3(8),4,6,16,18-hexaen-15-one
IUPAC Name:	(2S,9S,11S,12S)-2,7,17-trihydroxy-9-methoxypentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(20),3(8),4,6,16,18-hexaen-15-one
Synonyms:	Daldinone D
Standard InCHIKey:	GLJYOQVDANSTQF-NQANIHDXSA-N
Standard InCHI:	InChI=1S/C21H20O5/c1-26-17-9-13-10-5-7-15(23)20-16(24)8-6-12(18(10)20)21(13,25)11-3-2-4-14(22)19(11)17/h2-4,6,8,10,13,17,22,24-25H,5,7,9H2,1H3/t10-,13-,17-,21+/m0/s1
SMILES:	CO[C@H]1C[C@H]2[C@@H]3CCC(=O)C4=C(C=CC(=C34)[C@@]2(C5=C1C(=CC=C5)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44418836
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	=	41000	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 NPC477276 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	1436
0.2-0.3	2789
0.3-0.4	6922
0.4-0.5	11763
0.5-0.6	4640
0.6-0.7	7609
0.7-0.8	6281
0.8-0.85	846
0.85-0.9	35
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC162751
0.9189	High Similarity	NPC52161
0.9172	High Similarity	NPC477275
0.9128	High Similarity	NPC290695
0.9128	High Similarity	NPC106524
0.8912	High Similarity	NPC91019
0.8912	High Similarity	NPC106519
0.8725	High Similarity	NPC85310
0.8675	High Similarity	NPC34482
0.8618	High Similarity	NPC470570
0.8609	High Similarity	NPC193703
0.8609	High Similarity	NPC21599
0.8609	High Similarity	NPC48762
0.86	High Similarity	NPC469520
0.859	High Similarity	NPC474824
0.859	High Similarity	NPC470408
0.859	High Similarity	NPC182921
0.859	High Similarity	NPC218870
0.8571	High Similarity	NPC329933
0.8562	High Similarity	NPC478229
0.8553	High Similarity	NPC284495
0.8553	High Similarity	NPC478019
0.8535	High Similarity	NPC66029
0.8526	High Similarity	NPC478220
0.8516	High Similarity	NPC205766
0.85	High Similarity	NPC18380
0.85	High Similarity	NPC137232
0.8497	Intermediate Similarity	NPC147250
0.8481	Intermediate Similarity	NPC474861
0.8477	Intermediate Similarity	NPC474961
0.8467	Intermediate Similarity	NPC168471
0.8452	Intermediate Similarity	NPC477221
0.8452	Intermediate Similarity	NPC478219
0.8442	Intermediate Similarity	NPC119767
0.8442	Intermediate Similarity	NPC478018
0.8442	Intermediate Similarity	NPC34802
0.8438	Intermediate Similarity	NPC184326
0.8438	Intermediate Similarity	NPC292863
0.8431	Intermediate Similarity	NPC170055
0.8421	Intermediate Similarity	NPC451542
0.8421	Intermediate Similarity	NPC295712
0.8421	Intermediate Similarity	NPC296752
0.8421	Intermediate Similarity	NPC313047
0.8421	Intermediate Similarity	NPC474203
0.8418	Intermediate Similarity	NPC68727
0.8408	Intermediate Similarity	NPC51824
0.8408	Intermediate Similarity	NPC268992
0.8408	Intermediate Similarity	NPC113608
0.8408	Intermediate Similarity	NPC470338
0.8408	Intermediate Similarity	NPC470337
0.8397	Intermediate Similarity	NPC470568
0.8397	Intermediate Similarity	NPC315520
0.8397	Intermediate Similarity	NPC477914
0.8387	Intermediate Similarity	NPC142846
0.8385	Intermediate Similarity	NPC472261
0.8377	Intermediate Similarity	NPC285122
0.8377	Intermediate Similarity	NPC300540
0.8375	Intermediate Similarity	NPC195167
0.8375	Intermediate Similarity	NPC324736
0.8366	Intermediate Similarity	NPC84568
0.8366	Intermediate Similarity	NPC218866
0.8366	Intermediate Similarity	NPC48130
0.8366	Intermediate Similarity	NPC300684
0.8365	Intermediate Similarity	NPC478223
0.8355	Intermediate Similarity	NPC135524
0.8354	Intermediate Similarity	NPC329844
0.8354	Intermediate Similarity	NPC478218
0.8344	Intermediate Similarity	NPC474417
0.8344	Intermediate Similarity	NPC149526
0.8344	Intermediate Similarity	NPC470569
0.8344	Intermediate Similarity	NPC169452
0.8344	Intermediate Similarity	NPC478148
0.8344	Intermediate Similarity	NPC181560
0.8333	Intermediate Similarity	NPC20210
0.8333	Intermediate Similarity	NPC13715
0.8323	Intermediate Similarity	NPC215593
0.8323	Intermediate Similarity	NPC470810
0.8323	Intermediate Similarity	NPC472135
0.8323	Intermediate Similarity	NPC290194
0.8322	Intermediate Similarity	NPC191976
0.8313	Intermediate Similarity	NPC317580
0.8312	Intermediate Similarity	NPC471683
0.8302	Intermediate Similarity	NPC478133
0.8302	Intermediate Similarity	NPC66508
0.8302	Intermediate Similarity	NPC318270
0.8302	Intermediate Similarity	NPC226656
0.8301	Intermediate Similarity	NPC471682
0.8301	Intermediate Similarity	NPC66593
0.8301	Intermediate Similarity	NPC174905
0.8301	Intermediate Similarity	NPC293545
0.8291	Intermediate Similarity	NPC474534
0.8291	Intermediate Similarity	NPC470340
0.8291	Intermediate Similarity	NPC87708
0.8291	Intermediate Similarity	NPC180944
0.8291	Intermediate Similarity	NPC474533
0.8289	Intermediate Similarity	NPC305845
0.8289	Intermediate Similarity	NPC204045
0.8284	Intermediate Similarity	NPC70318
0.8282	Intermediate Similarity	NPC290160
0.8282	Intermediate Similarity	NPC476505
0.8282	Intermediate Similarity	NPC473009
0.828	Intermediate Similarity	NPC147735
0.828	Intermediate Similarity	NPC255641
0.828	Intermediate Similarity	NPC290954
0.828	Intermediate Similarity	NPC294646
0.828	Intermediate Similarity	NPC472633
0.8278	Intermediate Similarity	NPC138099
0.8278	Intermediate Similarity	NPC242994
0.8272	Intermediate Similarity	NPC478222
0.8272	Intermediate Similarity	NPC312273
0.8272	Intermediate Similarity	NPC301256
0.8269	Intermediate Similarity	NPC216624
0.8267	Intermediate Similarity	NPC301915
0.8267	Intermediate Similarity	NPC261292
0.8263	Intermediate Similarity	NPC470333
0.8261	Intermediate Similarity	NPC186113
0.8261	Intermediate Similarity	NPC326084
0.8261	Intermediate Similarity	NPC472617
0.8258	Intermediate Similarity	NPC472134
0.8258	Intermediate Similarity	NPC143685
0.8247	Intermediate Similarity	NPC42540
0.8247	Intermediate Similarity	NPC10764
0.8247	Intermediate Similarity	NPC471906
0.8247	Intermediate Similarity	NPC244691
0.8247	Intermediate Similarity	NPC227841
0.8247	Intermediate Similarity	NPC151607
0.8243	Intermediate Similarity	NPC267205
0.8243	Intermediate Similarity	NPC314048
0.8242	Intermediate Similarity	NPC225419
0.8239	Intermediate Similarity	NPC169990
0.8239	Intermediate Similarity	NPC210942
0.8239	Intermediate Similarity	NPC95842
0.8239	Intermediate Similarity	NPC474621
0.8239	Intermediate Similarity	NPC280530
0.8239	Intermediate Similarity	NPC474622
0.8239	Intermediate Similarity	NPC178964
0.8235	Intermediate Similarity	NPC193555
0.8235	Intermediate Similarity	NPC257644
0.8235	Intermediate Similarity	NPC232021
0.8235	Intermediate Similarity	NPC40118
0.8235	Intermediate Similarity	NPC126534
0.8235	Intermediate Similarity	NPC137649
0.8232	Intermediate Similarity	NPC478020
0.8232	Intermediate Similarity	NPC473010
0.8232	Intermediate Similarity	NPC478022
0.8231	Intermediate Similarity	NPC474517
0.8231	Intermediate Similarity	NPC72669
0.8228	Intermediate Similarity	NPC232645
0.8228	Intermediate Similarity	NPC476553
0.8228	Intermediate Similarity	NPC476552
0.8228	Intermediate Similarity	NPC72958
0.8228	Intermediate Similarity	NPC476551
0.8224	Intermediate Similarity	NPC96421
0.8221	Intermediate Similarity	NPC473961
0.8221	Intermediate Similarity	NPC315772
0.8221	Intermediate Similarity	NPC472402
0.8221	Intermediate Similarity	NPC473012
0.8221	Intermediate Similarity	NPC15374
0.8217	Intermediate Similarity	NPC473016
0.821	Intermediate Similarity	NPC472618
0.821	Intermediate Similarity	NPC475449
0.8205	Intermediate Similarity	NPC126767
0.8205	Intermediate Similarity	NPC289042
0.8205	Intermediate Similarity	NPC312929
0.8205	Intermediate Similarity	NPC475348
0.8205	Intermediate Similarity	NPC245584
0.8205	Intermediate Similarity	NPC261271
0.8205	Intermediate Similarity	NPC190648
0.8205	Intermediate Similarity	NPC56433
0.8205	Intermediate Similarity	NPC118027
0.82	Intermediate Similarity	NPC291454
0.8199	Intermediate Similarity	NPC272196
0.8193	Intermediate Similarity	NPC300307
0.8188	Intermediate Similarity	NPC282780
0.8188	Intermediate Similarity	NPC166480
0.8188	Intermediate Similarity	NPC287604
0.8188	Intermediate Similarity	NPC161964
0.8188	Intermediate Similarity	NPC472262
0.8187	Intermediate Similarity	NPC174599
0.8187	Intermediate Similarity	NPC82190
0.8187	Intermediate Similarity	NPC192219
0.8182	Intermediate Similarity	NPC53016
0.8182	Intermediate Similarity	NPC84266
0.8182	Intermediate Similarity	NPC251336
0.8182	Intermediate Similarity	NPC159721
0.8182	Intermediate Similarity	NPC297600
0.8182	Intermediate Similarity	NPC476473
0.8176	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC154683
0.8176	Intermediate Similarity	NPC43345
0.8176	Intermediate Similarity	NPC175738
0.8176	Intermediate Similarity	NPC474843
0.8171	Intermediate Similarity	NPC161151
0.817	Intermediate Similarity	NPC246638
0.817	Intermediate Similarity	NPC472603
0.817	Intermediate Similarity	NPC187843
0.817	Intermediate Similarity	NPC149533
0.817	Intermediate Similarity	NPC124365
0.817	Intermediate Similarity	NPC265178
0.8165	Intermediate Similarity	NPC227122

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 NPC477276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	921
0.2-0.3	1442
0.3-0.4	2620
0.4-0.5	2084
0.5-0.6	1182
0.6-0.7	459
0.7-0.8	114
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
0.8247	Intermediate Similarity	NPD7390	Discontinued
0.816	Intermediate Similarity	NPD6959	Discontinued
0.8079	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD5404	Approved
0.8026	Intermediate Similarity	NPD5406	Approved
0.8026	Intermediate Similarity	NPD5408	Approved
0.8026	Intermediate Similarity	NPD5405	Approved
0.7963	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1201	Approved
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7848	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4380	Phase 2
0.7823	Intermediate Similarity	NPD1470	Approved
0.7799	Intermediate Similarity	NPD6273	Approved
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7784	Intermediate Similarity	NPD6232	Discontinued
0.7736	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD1510	Phase 2
0.7714	Intermediate Similarity	NPD8150	Discontinued
0.7665	Intermediate Similarity	NPD5494	Approved
0.764	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1934	Approved
0.761	Intermediate Similarity	NPD7236	Approved
0.7597	Intermediate Similarity	NPD1607	Approved
0.7582	Intermediate Similarity	NPD1240	Approved
0.758	Intermediate Similarity	NPD1549	Phase 2
0.758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5761	Phase 2
0.7576	Intermediate Similarity	NPD5760	Phase 2
0.7561	Intermediate Similarity	NPD7411	Suspended
0.7558	Intermediate Similarity	NPD5844	Phase 1
0.7546	Intermediate Similarity	NPD3226	Approved
0.7534	Intermediate Similarity	NPD3019	Approved
0.7516	Intermediate Similarity	NPD6663	Approved
0.75	Intermediate Similarity	NPD3300	Phase 2
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD7003	Approved
0.7483	Intermediate Similarity	NPD5736	Approved
0.747	Intermediate Similarity	NPD2801	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7459	Intermediate Similarity	NPD6535	Approved
0.7452	Intermediate Similarity	NPD2796	Approved
0.7451	Intermediate Similarity	NPD3764	Approved
0.744	Intermediate Similarity	NPD7075	Discontinued
0.744	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2932	Approved
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7378	Intermediate Similarity	NPD7239	Suspended
0.7365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD943	Approved
0.7351	Intermediate Similarity	NPD3094	Phase 2
0.7351	Intermediate Similarity	NPD6778	Approved
0.7351	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD6782	Approved
0.7351	Intermediate Similarity	NPD6776	Approved
0.7351	Intermediate Similarity	NPD6781	Approved
0.7351	Intermediate Similarity	NPD6777	Approved
0.7351	Intermediate Similarity	NPD6780	Approved
0.7346	Intermediate Similarity	NPD1511	Approved
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD7699	Phase 2
0.7337	Intermediate Similarity	NPD7700	Phase 2
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1876	Approved
0.7279	Intermediate Similarity	NPD3091	Approved
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD3750	Approved
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1512	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7234	Intermediate Similarity	NPD7435	Discontinued
0.7234	Intermediate Similarity	NPD7697	Approved
0.7232	Intermediate Similarity	NPD6559	Discontinued
0.7216	Intermediate Similarity	NPD7074	Phase 3
0.7213	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6212	Phase 3
0.7213	Intermediate Similarity	NPD6213	Phase 3
0.7205	Intermediate Similarity	NPD2800	Approved
0.7202	Intermediate Similarity	NPD6801	Discontinued
0.72	Intermediate Similarity	NPD3818	Discontinued
0.72	Intermediate Similarity	NPD3092	Approved
0.7196	Intermediate Similarity	NPD8320	Phase 1
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD8319	Approved
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.719	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD2344	Approved
0.7176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD5711	Approved
0.716	Intermediate Similarity	NPD8166	Discontinued
0.7159	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7133	Intermediate Similarity	NPD3026	Approved
0.7133	Intermediate Similarity	NPD3023	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7125	Intermediate Similarity	NPD6100	Approved
0.7124	Intermediate Similarity	NPD1164	Approved
0.7119	Intermediate Similarity	NPD7472	Approved
0.7118	Intermediate Similarity	NPD3817	Phase 2
0.7118	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3024	Approved
0.7114	Intermediate Similarity	NPD3025	Approved
0.711	Intermediate Similarity	NPD8127	Discontinued
0.7102	Intermediate Similarity	NPD7799	Discontinued
0.7101	Intermediate Similarity	NPD37	Approved
0.7095	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6823	Phase 2
0.7083	Intermediate Similarity	NPD7028	Phase 2
0.7083	Intermediate Similarity	NPD7701	Phase 2
0.7083	Intermediate Similarity	NPD6599	Discontinued
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7078	Intermediate Similarity	NPD4624	Approved
0.7076	Intermediate Similarity	NPD7058	Phase 2
0.7076	Intermediate Similarity	NPD7057	Phase 3
0.7069	Intermediate Similarity	NPD3787	Discontinued
0.7068	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4059	Approved
0.7067	Intermediate Similarity	NPD3095	Discontinued
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7062	Intermediate Similarity	NPD7801	Approved
0.7059	Intermediate Similarity	NPD1283	Approved
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7039	Intermediate Similarity	NPD7251	Discontinued
0.703	Intermediate Similarity	NPD6799	Approved
0.7027	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD4140	Approved
0.7018	Intermediate Similarity	NPD5402	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD2309	Approved
0.7011	Intermediate Similarity	NPD7199	Phase 2
0.701	Intermediate Similarity	NPD7874	Approved
0.701	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD7177	Discontinued
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD7808	Phase 3
0.7	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6234	Discontinued
0.6977	Remote Similarity	NPD4967	Phase 2
0.6977	Remote Similarity	NPD4966	Approved
0.6977	Remote Similarity	NPD4965	Approved
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD5763	Approved
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.6971	Remote Similarity	NPD7229	Phase 3
0.6968	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3748	Approved
0.6943	Remote Similarity	NPD7008	Discontinued
0.694	Remote Similarity	NPD8434	Phase 2
0.6937	Remote Similarity	NPD6353	Approved
0.6933	Remote Similarity	NPD9545	Approved
0.6932	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3972	Approved
0.6918	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD3620	Phase 2
0.6914	Remote Similarity	NPD1551	Phase 2
0.6909	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4955	Approved
0.6906	Remote Similarity	NPD4954	Approved
0.6906	Remote Similarity	NPD36	Approved
0.6906	Remote Similarity	NPD5034	Approved
0.6906	Remote Similarity	NPD5026	Approved
0.6906	Remote Similarity	NPD5028	Approved
0.6905	Remote Similarity	NPD920	Approved
0.6899	Remote Similarity	NPD3268	Approved
0.6898	Remote Similarity	NPD4360	Phase 2

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