NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	460.21
Volume:	449.393
LogP:	3.466
LogD:	2.432
LogS:	-4.14
# Rotatable Bonds:	1
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	6.253
Fsp3:	0.72
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961
MDCK Permeability:	1.3357429452298675e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.463
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.897
30% Bioavailability (F30%):	0.257

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	85.61936950683594%
Volume Distribution (VD):	2.256
Pgp-substrate:	15.159652709960938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.21
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.521
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.747

ADMET: Excretion

Clearance (CL):	12.435
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.836
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.271
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.759

Download Data

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

Natural Product: NPC477670

Natural Product ID:	NPC477670
*Common Name:**	17-O-demethylaustalide B
IUPAC Name:	(1R,2R,4S,16R,17R,20S)-2,20-dihydroxy-13-methoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.01,17.04,16.06,14.08,12]tricosa-6(14),7,12-trien-11-one
Synonyms:
Standard InCHIKey:	ZFKOTULZHLMUJE-VCLZEFBQSA-N
Standard InCHI:	InChI=1S/C25H32O8/c1-12-14-11-30-20(27)17(14)19(29-6)13-9-15-22(4)7-8-24(28)32-21(2,3)25(22,33-24)16(26)10-23(15,5)31-18(12)13/h15-16,26,28H,7-11H2,1-6H3/t15-,16-,22-,23+,24+,25-/m1/s1
SMILES:	CC1=C2COC(=O)C2=C(C3=C1O[C@]4(C[C@H]([C@@]56[C@@]([C@H]4C3)(CC[C@@](O5)(OC6(C)C)O)C)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118706612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	Lazurnaya Bay, the Sea of Japan	n.a.	PMID[24852445]
NPO33623	Penicillium lividum	Species	Aspergillaceae	Eukaryota	n.a.	isolated from superficial mycobiota of the brown alga Sargassum miyabei (Lazurnaya Bay, the Sea of Japan)	n.a.	PMID[24852445]
NPO29375	Penicillium thomii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	250000	nM	PMID[24852445]

☑ 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 NPC477670 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	388
0.1-0.2	1656
0.2-0.3	3402
0.3-0.4	6188
0.4-0.5	10127
0.5-0.6	7782
0.6-0.7	6785
0.7-0.8	6058
0.8-0.85	278
0.85-0.9	29
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9245	High Similarity	NPC477671
0.9245	High Similarity	NPC477687
0.9068	High Similarity	NPC477674
0.9068	High Similarity	NPC477675
0.9057	High Similarity	NPC477673
0.9057	High Similarity	NPC477672
0.8944	High Similarity	NPC477669
0.883	High Similarity	NPC324220
0.883	High Similarity	NPC312630
0.8817	High Similarity	NPC477571
0.8817	High Similarity	NPC477573
0.8817	High Similarity	NPC477572
0.8772	High Similarity	NPC294149
0.8758	High Similarity	NPC477676
0.875	High Similarity	NPC472621
0.8728	High Similarity	NPC473607
0.8728	High Similarity	NPC473729
0.8698	High Similarity	NPC472622
0.8675	High Similarity	NPC470358
0.8655	High Similarity	NPC472620
0.8647	High Similarity	NPC473202
0.8634	High Similarity	NPC470359
0.8631	High Similarity	NPC478044
0.8629	High Similarity	NPC475656
0.8629	High Similarity	NPC475148
0.8621	High Similarity	NPC245059
0.8621	High Similarity	NPC84494
0.8613	High Similarity	NPC472661
0.858	High Similarity	NPC472663
0.858	High Similarity	NPC472662
0.8571	High Similarity	NPC470453
0.8571	High Similarity	NPC164047
0.8571	High Similarity	NPC470452
0.8571	High Similarity	NPC470448
0.8563	High Similarity	NPC233978
0.8555	High Similarity	NPC470454
0.8555	High Similarity	NPC199533
0.8555	High Similarity	NPC63105
0.8555	High Similarity	NPC162248
0.8538	High Similarity	NPC472619
0.8538	High Similarity	NPC102810
0.8506	High Similarity	NPC98943
0.8506	High Similarity	NPC475233
0.8497	Intermediate Similarity	NPC476311
0.8488	Intermediate Similarity	NPC298778
0.8471	Intermediate Similarity	NPC21016
0.8471	Intermediate Similarity	NPC102372
0.8471	Intermediate Similarity	NPC146584
0.8466	Intermediate Similarity	NPC477860
0.8466	Intermediate Similarity	NPC475161
0.8448	Intermediate Similarity	NPC474345
0.8448	Intermediate Similarity	NPC68381
0.843	Intermediate Similarity	NPC213416
0.843	Intermediate Similarity	NPC191653
0.8418	Intermediate Similarity	NPC473883
0.8412	Intermediate Similarity	NPC208120
0.8412	Intermediate Similarity	NPC173587
0.8412	Intermediate Similarity	NPC17432
0.8407	Intermediate Similarity	NPC314687
0.8405	Intermediate Similarity	NPC472345
0.84	Intermediate Similarity	NPC46958
0.84	Intermediate Similarity	NPC227275
0.8393	Intermediate Similarity	NPC218818
0.8393	Intermediate Similarity	NPC478042
0.8393	Intermediate Similarity	NPC239118
0.8393	Intermediate Similarity	NPC4950
0.8393	Intermediate Similarity	NPC279732
0.8391	Intermediate Similarity	NPC98776
0.8391	Intermediate Similarity	NPC213052
0.8382	Intermediate Similarity	NPC241874
0.8372	Intermediate Similarity	NPC232936
0.8372	Intermediate Similarity	NPC249977
0.8362	Intermediate Similarity	NPC208069
0.8352	Intermediate Similarity	NPC476210
0.8352	Intermediate Similarity	NPC476199
0.8343	Intermediate Similarity	NPC472055
0.8343	Intermediate Similarity	NPC146803
0.8333	Intermediate Similarity	NPC5029
0.8333	Intermediate Similarity	NPC271385
0.8333	Intermediate Similarity	NPC111536
0.8333	Intermediate Similarity	NPC30432
0.8333	Intermediate Similarity	NPC169018
0.8333	Intermediate Similarity	NPC76128
0.8324	Intermediate Similarity	NPC259905
0.8324	Intermediate Similarity	NPC473686
0.8324	Intermediate Similarity	NPC221140
0.8324	Intermediate Similarity	NPC475352
0.8324	Intermediate Similarity	NPC229817
0.8324	Intermediate Similarity	NPC475220
0.8315	Intermediate Similarity	NPC293227
0.8315	Intermediate Similarity	NPC475662
0.8315	Intermediate Similarity	NPC473717
0.8315	Intermediate Similarity	NPC473631
0.8314	Intermediate Similarity	NPC178851
0.8314	Intermediate Similarity	NPC125465
0.8314	Intermediate Similarity	NPC472452
0.8304	Intermediate Similarity	NPC120012
0.8304	Intermediate Similarity	NPC29055
0.8304	Intermediate Similarity	NPC475055
0.8295	Intermediate Similarity	NPC478050
0.8295	Intermediate Similarity	NPC475246
0.8294	Intermediate Similarity	NPC117985
0.8294	Intermediate Similarity	NPC478041
0.8286	Intermediate Similarity	NPC476139
0.8284	Intermediate Similarity	NPC470339
0.8282	Intermediate Similarity	NPC470357
0.8276	Intermediate Similarity	NPC313717
0.8276	Intermediate Similarity	NPC251144
0.8276	Intermediate Similarity	NPC241387
0.8276	Intermediate Similarity	NPC315306
0.8274	Intermediate Similarity	NPC164427
0.8266	Intermediate Similarity	NPC225419
0.8266	Intermediate Similarity	NPC474024
0.8266	Intermediate Similarity	NPC473094
0.8258	Intermediate Similarity	NPC188217
0.8256	Intermediate Similarity	NPC475979
0.8256	Intermediate Similarity	NPC222531
0.8256	Intermediate Similarity	NPC7752
0.8251	Intermediate Similarity	NPC314020
0.8249	Intermediate Similarity	NPC80360
0.8249	Intermediate Similarity	NPC35266
0.8246	Intermediate Similarity	NPC473961
0.8246	Intermediate Similarity	NPC473022
0.8246	Intermediate Similarity	NPC472402
0.8242	Intermediate Similarity	NPC478034
0.8242	Intermediate Similarity	NPC48474
0.8239	Intermediate Similarity	NPC3718
0.8235	Intermediate Similarity	NPC470810
0.8232	Intermediate Similarity	NPC8817
0.8229	Intermediate Similarity	NPC474075
0.8229	Intermediate Similarity	NPC38438
0.8229	Intermediate Similarity	NPC471920
0.8229	Intermediate Similarity	NPC148185
0.8229	Intermediate Similarity	NPC20114
0.8229	Intermediate Similarity	NPC129930
0.8229	Intermediate Similarity	NPC292712
0.8229	Intermediate Similarity	NPC114550
0.8229	Intermediate Similarity	NPC471922
0.8229	Intermediate Similarity	NPC471921
0.8229	Intermediate Similarity	NPC118128
0.8229	Intermediate Similarity	NPC312006
0.8225	Intermediate Similarity	NPC158542
0.8222	Intermediate Similarity	NPC241847
0.8218	Intermediate Similarity	NPC473096
0.8218	Intermediate Similarity	NPC473095
0.8214	Intermediate Similarity	NPC175192
0.8212	Intermediate Similarity	NPC478001
0.8208	Intermediate Similarity	NPC173292
0.8207	Intermediate Similarity	NPC470195
0.8207	Intermediate Similarity	NPC470197
0.8207	Intermediate Similarity	NPC470200
0.8207	Intermediate Similarity	NPC470193
0.8207	Intermediate Similarity	NPC470198
0.8207	Intermediate Similarity	NPC316274
0.8207	Intermediate Similarity	NPC470196
0.8207	Intermediate Similarity	NPC282474
0.8207	Intermediate Similarity	NPC470194
0.8204	Intermediate Similarity	NPC167903
0.8204	Intermediate Similarity	NPC473509
0.8204	Intermediate Similarity	NPC477961
0.8204	Intermediate Similarity	NPC475131
0.8204	Intermediate Similarity	NPC477960
0.8204	Intermediate Similarity	NPC477962
0.8204	Intermediate Similarity	NPC473770
0.8202	Intermediate Similarity	NPC195114
0.8202	Intermediate Similarity	NPC275690
0.8202	Intermediate Similarity	NPC212290
0.8202	Intermediate Similarity	NPC161609
0.8198	Intermediate Similarity	NPC100849
0.8193	Intermediate Similarity	NPC179178
0.8192	Intermediate Similarity	NPC475054
0.8192	Intermediate Similarity	NPC156635
0.8187	Intermediate Similarity	NPC314672
0.8187	Intermediate Similarity	NPC69868
0.8187	Intermediate Similarity	NPC65746
0.8182	Intermediate Similarity	NPC475080
0.8182	Intermediate Similarity	NPC472054
0.8182	Intermediate Similarity	NPC476152
0.8177	Intermediate Similarity	NPC174486
0.8177	Intermediate Similarity	NPC105591
0.8176	Intermediate Similarity	NPC50430
0.8176	Intermediate Similarity	NPC472617
0.8171	Intermediate Similarity	NPC17219
0.8167	Intermediate Similarity	NPC167045
0.8167	Intermediate Similarity	NPC114120
0.8167	Intermediate Similarity	NPC106700
0.8166	Intermediate Similarity	NPC17521
0.8161	Intermediate Similarity	NPC117854
0.8161	Intermediate Similarity	NPC471180
0.8161	Intermediate Similarity	NPC472660
0.8161	Intermediate Similarity	NPC477154
0.8161	Intermediate Similarity	NPC6588
0.816	Intermediate Similarity	NPC112749
0.8155	Intermediate Similarity	NPC472799
0.8155	Intermediate Similarity	NPC273248
0.8152	Intermediate Similarity	NPC476358
0.815	Intermediate Similarity	NPC294722
0.815	Intermediate Similarity	NPC99216
0.815	Intermediate Similarity	NPC473286
0.815	Intermediate Similarity	NPC473908

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 NPC477670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	1028
0.2-0.3	2179
0.3-0.4	2601
0.4-0.5	1835
0.5-0.6	806
0.6-0.7	257
0.7-0.8	112
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.811	Intermediate Similarity	NPD2534	Approved
0.811	Intermediate Similarity	NPD2532	Approved
0.811	Intermediate Similarity	NPD2533	Approved
0.7955	Intermediate Similarity	NPD7228	Approved
0.7941	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD5494	Approved
0.791	Intermediate Similarity	NPD5844	Phase 1
0.788	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.7874	Intermediate Similarity	NPD6959	Discontinued
0.7865	Intermediate Similarity	NPD7074	Phase 3
0.7849	Intermediate Similarity	NPD4965	Approved
0.7849	Intermediate Similarity	NPD4966	Approved
0.7849	Intermediate Similarity	NPD4967	Phase 2
0.7809	Intermediate Similarity	NPD7054	Approved
0.7809	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7473	Discontinued
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD7240	Approved
0.7765	Intermediate Similarity	NPD7472	Approved
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7753	Intermediate Similarity	NPD3818	Discontinued
0.7735	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6232	Discontinued
0.7701	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7075	Discontinued
0.768	Intermediate Similarity	NPD7251	Discontinued
0.7674	Intermediate Similarity	NPD37	Approved
0.767	Intermediate Similarity	NPD7199	Phase 2
0.7644	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD7808	Phase 3
0.763	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5711	Approved
0.7627	Intermediate Similarity	NPD5710	Approved
0.7624	Intermediate Similarity	NPD6797	Phase 2
0.7609	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2800	Approved
0.7572	Intermediate Similarity	NPD6801	Discontinued
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7563	Intermediate Similarity	NPD7783	Phase 2
0.7563	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6599	Discontinued
0.7558	Intermediate Similarity	NPD4380	Phase 2
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7542	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3817	Phase 2
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7471	Intermediate Similarity	NPD1934	Approved
0.7439	Intermediate Similarity	NPD6651	Approved
0.743	Intermediate Similarity	NPD3787	Discontinued
0.7414	Intermediate Similarity	NPD7411	Suspended
0.7386	Intermediate Similarity	NPD5402	Approved
0.7381	Intermediate Similarity	NPD6674	Discontinued
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7363	Intermediate Similarity	NPD3751	Discontinued
0.736	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4628	Phase 3
0.733	Intermediate Similarity	NPD2801	Approved
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.7303	Intermediate Similarity	NPD3749	Approved
0.7301	Intermediate Similarity	NPD7985	Registered
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.725	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD3882	Suspended
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8455	Phase 2
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7209	Intermediate Similarity	NPD6799	Approved
0.7202	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD6099	Approved
0.72	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7871	Phase 2
0.7172	Intermediate Similarity	NPD7870	Phase 2
0.7172	Intermediate Similarity	NPD8320	Phase 1
0.7172	Intermediate Similarity	NPD8319	Approved
0.7168	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6823	Phase 2
0.7151	Intermediate Similarity	NPD7768	Phase 2
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7129	Intermediate Similarity	NPD7801	Approved
0.7112	Intermediate Similarity	NPD7685	Pre-registration
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5403	Approved
0.7086	Intermediate Similarity	NPD920	Approved
0.7069	Intermediate Similarity	NPD5401	Approved
0.7066	Intermediate Similarity	NPD5124	Phase 1
0.7066	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5760	Phase 2
0.7039	Intermediate Similarity	NPD5761	Phase 2
0.7035	Intermediate Similarity	NPD7680	Approved
0.7029	Intermediate Similarity	NPD6273	Approved
0.7024	Intermediate Similarity	NPD7930	Approved
0.7018	Intermediate Similarity	NPD1549	Phase 2
0.7011	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD2796	Approved
0.6989	Remote Similarity	NPD7799	Discontinued
0.6986	Remote Similarity	NPD8366	Approved
0.6978	Remote Similarity	NPD919	Approved
0.6936	Remote Similarity	NPD3750	Approved
0.6934	Remote Similarity	NPD8491	Approved
0.6932	Remote Similarity	NPD1512	Approved
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8407	Phase 2
0.6911	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD1247	Approved
0.6901	Remote Similarity	NPD2935	Discontinued
0.6886	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7999	Approved
0.6879	Remote Similarity	NPD1243	Approved
0.6875	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1653	Approved
0.6847	Remote Similarity	NPD7584	Approved
0.6842	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD8368	Discontinued
0.6842	Remote Similarity	NPD2799	Discontinued
0.6839	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6213	Phase 3
0.6837	Remote Similarity	NPD6212	Phase 3
0.6834	Remote Similarity	NPD8285	Discontinued
0.6828	Remote Similarity	NPD3926	Phase 2
0.6822	Remote Similarity	NPD8469	Approved
0.6818	Remote Similarity	NPD7390	Discontinued
0.6816	Remote Similarity	NPD5006	Approved
0.6816	Remote Similarity	NPD5005	Approved
0.6802	Remote Similarity	NPD1551	Phase 2
0.6794	Remote Similarity	NPD8404	Phase 2
0.6786	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7097	Phase 1
0.6782	Remote Similarity	NPD7497	Discontinued
0.6782	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7286	Phase 2
0.6765	Remote Similarity	NPD7583	Approved
0.6761	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1510	Phase 2
0.6743	Remote Similarity	NPD7003	Approved
0.674	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7585	Approved
0.6728	Remote Similarity	NPD8067	Phase 3
0.6725	Remote Similarity	NPD1607	Approved
0.6719	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2403	Approved
0.6702	Remote Similarity	NPD5953	Discontinued
0.67	Remote Similarity	NPD4420	Approved
0.6686	Remote Similarity	NPD2313	Discontinued
0.6685	Remote Similarity	NPD7028	Phase 2
0.6684	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD8059	Phase 3

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