NPASS Compound

Structure

NPC192999 OpenBabel07101718222D 30 31 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 8.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8660 6.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 7.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 18 2 0 0 0 0 6 29 1 0 0 0 0 7 24 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 1 0 0 0 20 23 1 1 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 6 0 0 0 24 28 1 0 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.29
Volume:	457.248
LogP:	4.038
LogD:	4.015
LogS:	-4.836
# Rotatable Bonds:	11
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.428
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.761
MDCK Permeability:	3.495071723591536e-05
Pgp-inhibitor:	0.676
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.792
Plasma Protein Binding (PPB):	67.70510864257812%
Volume Distribution (VD):	0.413
Pgp-substrate:	32.88896560668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.26
CYP2C19-inhibitor:	0.237
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.278
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	5.682
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.217
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.589
Carcinogencity:	0.191
Eye Corrosion:	0.026
Eye Irritation:	0.092
Respiratory Toxicity:	0.812

Download Data

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

Natural Product: NPC192999

Natural Product ID:	NPC192999
*Common Name:**	Abiesadine Y
IUPAC Name:	4-O-[[(1R,4aR,5S,8aR)-5-[(3S)-3-hydroxy-3-methylpent-4-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl] 1-O-methyl butanedioate
Synonyms:
Standard InCHIKey:	YBZFNTOZFZILEJ-KJNIBPJZSA-N
Standard InCHI:	InChI=1S/C25H40O5/c1-7-24(4,28)16-13-19-18(2)9-10-20-23(3,14-8-15-25(19,20)5)17-30-22(27)12-11-21(26)29-6/h7,19-20,28H,1-2,8-17H2,3-6H3/t19-,20-,23-,24+,25+/m0/s1
SMILES:	C=C[C@](C)(CC[C@H]1C(=C)CC[C@H]2[C@@](C)(CCC[C@]12C)COC(=O)CCC(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL605359
PubChem CID:	46230265
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	48.5	ug.mL-1	PMID[506984]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	10.6	ug.mL-1	PMID[506984]
NPT2	Others	Unspecified		IC50	=	22.4	ug.mL-1	PMID[506984]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[506984]

☑ 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 NPC192999 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	162
0.1-0.2	1193
0.2-0.3	5175
0.3-0.4	15422
0.4-0.5	8041
0.5-0.6	7505
0.6-0.7	4642
0.7-0.8	533
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476438
0.8553	High Similarity	NPC18819
0.8553	High Similarity	NPC46610
0.8313	Intermediate Similarity	NPC30984
0.8313	Intermediate Similarity	NPC164424
0.8276	Intermediate Similarity	NPC476416
0.8171	Intermediate Similarity	NPC471159
0.8171	Intermediate Similarity	NPC123880
0.8171	Intermediate Similarity	NPC15910
0.8161	Intermediate Similarity	NPC476417
0.8125	Intermediate Similarity	NPC247783
0.8125	Intermediate Similarity	NPC269543
0.8108	Intermediate Similarity	NPC476406
0.8101	Intermediate Similarity	NPC476601
0.8072	Intermediate Similarity	NPC476927
0.8049	Intermediate Similarity	NPC327002
0.8049	Intermediate Similarity	NPC14203
0.8049	Intermediate Similarity	NPC229584
0.8	Intermediate Similarity	NPC238227
0.7978	Intermediate Similarity	NPC476415
0.7976	Intermediate Similarity	NPC102048
0.7952	Intermediate Similarity	NPC475395
0.7952	Intermediate Similarity	NPC476984
0.7922	Intermediate Similarity	NPC91369
0.7907	Intermediate Similarity	NPC128644
0.7901	Intermediate Similarity	NPC239098
0.7901	Intermediate Similarity	NPC179028
0.7901	Intermediate Similarity	NPC321514
0.7895	Intermediate Similarity	NPC290445
0.7895	Intermediate Similarity	NPC36616
0.7882	Intermediate Similarity	NPC329738
0.7882	Intermediate Similarity	NPC476602
0.7848	Intermediate Similarity	NPC71152
0.7841	Intermediate Similarity	NPC232202
0.7841	Intermediate Similarity	NPC214844
0.7831	Intermediate Similarity	NPC170303
0.7831	Intermediate Similarity	NPC232625
0.7821	Intermediate Similarity	NPC72343
0.7808	Intermediate Similarity	NPC41160
0.7805	Intermediate Similarity	NPC100906
0.7805	Intermediate Similarity	NPC327674
0.7792	Intermediate Similarity	NPC9942
0.7791	Intermediate Similarity	NPC329692
0.7791	Intermediate Similarity	NPC185638
0.7791	Intermediate Similarity	NPC476104
0.7778	Intermediate Similarity	NPC469867
0.7738	Intermediate Similarity	NPC2524
0.7738	Intermediate Similarity	NPC474605
0.7738	Intermediate Similarity	NPC476292
0.7717	Intermediate Similarity	NPC107243
0.7711	Intermediate Similarity	NPC170038
0.7683	Intermediate Similarity	NPC476986
0.7683	Intermediate Similarity	NPC470905
0.7674	Intermediate Similarity	NPC269638
0.7674	Intermediate Similarity	NPC471344
0.7667	Intermediate Similarity	NPC151722
0.7647	Intermediate Similarity	NPC471037
0.7647	Intermediate Similarity	NPC312480
0.7647	Intermediate Similarity	NPC473592
0.7647	Intermediate Similarity	NPC243347
0.7647	Intermediate Similarity	NPC49208
0.7647	Intermediate Similarity	NPC23748
0.764	Intermediate Similarity	NPC471371
0.764	Intermediate Similarity	NPC471370
0.7619	Intermediate Similarity	NPC40228
0.7619	Intermediate Similarity	NPC223330
0.7619	Intermediate Similarity	NPC48673
0.7619	Intermediate Similarity	NPC20096
0.7619	Intermediate Similarity	NPC142163
0.7619	Intermediate Similarity	NPC209318
0.7614	Intermediate Similarity	NPC291665
0.7614	Intermediate Similarity	NPC255176
0.7614	Intermediate Similarity	NPC472870
0.759	Intermediate Similarity	NPC242767
0.759	Intermediate Similarity	NPC263951
0.759	Intermediate Similarity	NPC118987
0.7586	Intermediate Similarity	NPC73038
0.7586	Intermediate Similarity	NPC322159
0.7586	Intermediate Similarity	NPC472505
0.7586	Intermediate Similarity	NPC324063
0.7586	Intermediate Similarity	NPC475007
0.7561	Intermediate Similarity	NPC283619
0.7561	Intermediate Similarity	NPC61952
0.7561	Intermediate Similarity	NPC474433
0.7561	Intermediate Similarity	NPC132542
0.7558	Intermediate Similarity	NPC156981
0.7558	Intermediate Similarity	NPC263974
0.7558	Intermediate Similarity	NPC306951
0.7556	Intermediate Similarity	NPC471747
0.7556	Intermediate Similarity	NPC160506
0.7556	Intermediate Similarity	NPC198054
0.7531	Intermediate Similarity	NPC39362
0.7531	Intermediate Similarity	NPC476844
0.7529	Intermediate Similarity	NPC256112
0.7528	Intermediate Similarity	NPC469866
0.7528	Intermediate Similarity	NPC253618
0.7528	Intermediate Similarity	NPC50488
0.7528	Intermediate Similarity	NPC16265
0.7528	Intermediate Similarity	NPC77001
0.7528	Intermediate Similarity	NPC474396
0.7528	Intermediate Similarity	NPC194642
0.7528	Intermediate Similarity	NPC471342
0.7527	Intermediate Similarity	NPC170131
0.7527	Intermediate Similarity	NPC57416
0.75	Intermediate Similarity	NPC477926
0.75	Intermediate Similarity	NPC206735
0.75	Intermediate Similarity	NPC476265
0.75	Intermediate Similarity	NPC167877
0.75	Intermediate Similarity	NPC281880
0.75	Intermediate Similarity	NPC274522
0.75	Intermediate Similarity	NPC290481
0.75	Intermediate Similarity	NPC474768
0.75	Intermediate Similarity	NPC166857
0.75	Intermediate Similarity	NPC104545
0.75	Intermediate Similarity	NPC37038
0.75	Intermediate Similarity	NPC134067
0.75	Intermediate Similarity	NPC472813
0.75	Intermediate Similarity	NPC53565
0.7474	Intermediate Similarity	NPC115862
0.7473	Intermediate Similarity	NPC267266
0.7473	Intermediate Similarity	NPC470656
0.7473	Intermediate Similarity	NPC474835
0.7473	Intermediate Similarity	NPC199543
0.7473	Intermediate Similarity	NPC277721
0.7473	Intermediate Similarity	NPC147272
0.7471	Intermediate Similarity	NPC65661
0.7471	Intermediate Similarity	NPC76333
0.7471	Intermediate Similarity	NPC52628
0.7471	Intermediate Similarity	NPC283733
0.747	Intermediate Similarity	NPC198240
0.7468	Intermediate Similarity	NPC235586
0.7447	Intermediate Similarity	NPC316598
0.7444	Intermediate Similarity	NPC153853
0.7444	Intermediate Similarity	NPC48732
0.7444	Intermediate Similarity	NPC472866
0.7442	Intermediate Similarity	NPC474789
0.7442	Intermediate Similarity	NPC311070
0.7442	Intermediate Similarity	NPC79945
0.7442	Intermediate Similarity	NPC52108
0.7439	Intermediate Similarity	NPC476985
0.7439	Intermediate Similarity	NPC474316
0.7439	Intermediate Similarity	NPC475744
0.7439	Intermediate Similarity	NPC104806
0.7419	Intermediate Similarity	NPC116457
0.7419	Intermediate Similarity	NPC327179
0.7419	Intermediate Similarity	NPC235053
0.7416	Intermediate Similarity	NPC263079
0.7416	Intermediate Similarity	NPC229407
0.7416	Intermediate Similarity	NPC160304
0.7416	Intermediate Similarity	NPC48824
0.7416	Intermediate Similarity	NPC104560
0.7416	Intermediate Similarity	NPC254572
0.7416	Intermediate Similarity	NPC250687
0.7412	Intermediate Similarity	NPC77003
0.7412	Intermediate Similarity	NPC474955
0.7412	Intermediate Similarity	NPC90055
0.7412	Intermediate Similarity	NPC476101
0.7412	Intermediate Similarity	NPC159148
0.7407	Intermediate Similarity	NPC161923
0.7407	Intermediate Similarity	NPC237591
0.7407	Intermediate Similarity	NPC283908
0.7407	Intermediate Similarity	NPC3753
0.7407	Intermediate Similarity	NPC255168
0.7407	Intermediate Similarity	NPC183503
0.7407	Intermediate Similarity	NPC103958
0.7407	Intermediate Similarity	NPC166797
0.7391	Intermediate Similarity	NPC159410
0.7391	Intermediate Similarity	NPC57117
0.7386	Intermediate Similarity	NPC472869
0.7386	Intermediate Similarity	NPC322922
0.7386	Intermediate Similarity	NPC70661
0.7386	Intermediate Similarity	NPC321812
0.7386	Intermediate Similarity	NPC85698
0.7386	Intermediate Similarity	NPC262085
0.7386	Intermediate Similarity	NPC187545
0.7386	Intermediate Similarity	NPC82979
0.7386	Intermediate Similarity	NPC476982
0.7386	Intermediate Similarity	NPC168231
0.7386	Intermediate Similarity	NPC9231
0.7386	Intermediate Similarity	NPC175145
0.7386	Intermediate Similarity	NPC325594
0.7386	Intermediate Similarity	NPC473226
0.7386	Intermediate Similarity	NPC475069
0.7381	Intermediate Similarity	NPC231431
0.7363	Intermediate Similarity	NPC470113
0.7363	Intermediate Similarity	NPC154101
0.7363	Intermediate Similarity	NPC177641
0.7363	Intermediate Similarity	NPC473986
0.7363	Intermediate Similarity	NPC474018
0.7363	Intermediate Similarity	NPC72845
0.7356	Intermediate Similarity	NPC194937
0.7356	Intermediate Similarity	NPC476038
0.7356	Intermediate Similarity	NPC130966
0.7356	Intermediate Similarity	NPC165064
0.7349	Intermediate Similarity	NPC66105
0.734	Intermediate Similarity	NPC254496
0.734	Intermediate Similarity	NPC475894
0.7333	Intermediate Similarity	NPC269267
0.7333	Intermediate Similarity	NPC262043
0.7333	Intermediate Similarity	NPC174342

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 NPC192999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1624
0.2-0.3	3915
0.3-0.4	2367
0.4-0.5	649
0.5-0.6	275
0.6-0.7	173
0.7-0.8	6
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
0.7667	Intermediate Similarity	NPD6399	Phase 3
0.7556	Intermediate Similarity	NPD8035	Phase 2
0.7556	Intermediate Similarity	NPD8034	Phase 2
0.734	Intermediate Similarity	NPD7902	Approved
0.7174	Intermediate Similarity	NPD7637	Suspended
0.7126	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4225	Approved
0.7021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7748	Approved
0.7021	Intermediate Similarity	NPD7900	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD6084	Phase 2
0.6979	Remote Similarity	NPD6083	Phase 2
0.6966	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5696	Approved
0.6907	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6695	Phase 3
0.6848	Remote Similarity	NPD5737	Approved
0.6848	Remote Similarity	NPD6672	Approved
0.6827	Remote Similarity	NPD6650	Approved
0.6827	Remote Similarity	NPD6649	Approved
0.6813	Remote Similarity	NPD6409	Approved
0.6813	Remote Similarity	NPD7521	Approved
0.6813	Remote Similarity	NPD5330	Approved
0.6813	Remote Similarity	NPD6684	Approved
0.6813	Remote Similarity	NPD7146	Approved
0.6813	Remote Similarity	NPD7334	Approved
0.6809	Remote Similarity	NPD5284	Approved
0.6809	Remote Similarity	NPD6411	Approved
0.6809	Remote Similarity	NPD7515	Phase 2
0.6809	Remote Similarity	NPD5281	Approved
0.6796	Remote Similarity	NPD6373	Approved
0.6796	Remote Similarity	NPD6372	Approved
0.6774	Remote Similarity	NPD6051	Approved
0.6771	Remote Similarity	NPD5695	Phase 3
0.6737	Remote Similarity	NPD5778	Approved
0.6737	Remote Similarity	NPD5779	Approved
0.6705	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4821	Approved
0.6705	Remote Similarity	NPD4819	Approved
0.6705	Remote Similarity	NPD7525	Registered
0.6705	Remote Similarity	NPD4820	Approved
0.6705	Remote Similarity	NPD4822	Approved
0.6699	Remote Similarity	NPD6881	Approved
0.6699	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4623	Approved
0.663	Remote Similarity	NPD6098	Approved
0.663	Remote Similarity	NPD4519	Discontinued
0.6602	Remote Similarity	NPD5697	Approved
0.6598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6080	Approved
0.6596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6673	Approved
0.6596	Remote Similarity	NPD6904	Approved
0.6596	Remote Similarity	NPD6101	Approved
0.6593	Remote Similarity	NPD4786	Approved
0.6588	Remote Similarity	NPD6926	Approved
0.6588	Remote Similarity	NPD6924	Approved
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.6566	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7524	Approved
0.6559	Remote Similarity	NPD7750	Discontinued
0.6559	Remote Similarity	NPD3573	Approved
0.6556	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD6686	Approved
0.6538	Remote Similarity	NPD6011	Approved
0.6522	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6931	Approved
0.6517	Remote Similarity	NPD4695	Discontinued
0.6517	Remote Similarity	NPD6930	Phase 2
0.6514	Remote Similarity	NPD7115	Discovery
0.6512	Remote Similarity	NPD3702	Approved
0.6512	Remote Similarity	NPD8039	Approved
0.6509	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD6617	Approved
0.6509	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD8130	Phase 1
0.6484	Remote Similarity	NPD5362	Discontinued
0.6484	Remote Similarity	NPD7154	Phase 3
0.6477	Remote Similarity	NPD4271	Approved
0.6477	Remote Similarity	NPD4268	Approved
0.6477	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6014	Approved
0.6476	Remote Similarity	NPD6012	Approved
0.6476	Remote Similarity	NPD6013	Approved
0.6458	Remote Similarity	NPD5693	Phase 1
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD5786	Approved
0.6449	Remote Similarity	NPD6882	Approved
0.6449	Remote Similarity	NPD8297	Approved
0.6444	Remote Similarity	NPD5369	Approved
0.6442	Remote Similarity	NPD5701	Approved
0.6437	Remote Similarity	NPD6933	Approved
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.6421	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3665	Phase 1
0.6413	Remote Similarity	NPD3666	Approved
0.6413	Remote Similarity	NPD3133	Approved
0.6404	Remote Similarity	NPD4195	Approved
0.6404	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD6929	Approved
0.6395	Remote Similarity	NPD4785	Approved
0.6395	Remote Similarity	NPD4784	Approved
0.6374	Remote Similarity	NPD4269	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6374	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD6435	Approved
0.6373	Remote Similarity	NPD5211	Phase 2
0.6373	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD6116	Phase 1
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5785	Approved
0.6354	Remote Similarity	NPD5207	Approved
0.6353	Remote Similarity	NPD4243	Approved
0.6344	Remote Similarity	NPD1694	Approved
0.6344	Remote Similarity	NPD5329	Approved
0.6333	Remote Similarity	NPD7509	Discontinued
0.6333	Remote Similarity	NPD7332	Phase 2
0.6333	Remote Similarity	NPD7514	Phase 3
0.6322	Remote Similarity	NPD6942	Approved
0.6322	Remote Similarity	NPD7339	Approved
0.6322	Remote Similarity	NPD8264	Approved
0.6316	Remote Similarity	NPD5208	Approved
0.6304	Remote Similarity	NPD5331	Approved
0.6304	Remote Similarity	NPD5332	Approved
0.6292	Remote Similarity	NPD7145	Approved
0.6289	Remote Similarity	NPD6079	Approved
0.6289	Remote Similarity	NPD5694	Approved
0.6289	Remote Similarity	NPD6050	Approved
0.6289	Remote Similarity	NPD7087	Discontinued
0.6277	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5344	Discontinued
0.6264	Remote Similarity	NPD4790	Discontinued
0.6263	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD5141	Approved
0.6239	Remote Similarity	NPD8133	Approved
0.6237	Remote Similarity	NPD3668	Phase 3
0.6237	Remote Similarity	NPD4197	Approved
0.6237	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7144	Approved
0.6235	Remote Similarity	NPD7143	Approved
0.6224	Remote Similarity	NPD4202	Approved
0.6211	Remote Similarity	NPD4251	Approved
0.6211	Remote Similarity	NPD4250	Approved
0.6207	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4697	Phase 3
0.619	Remote Similarity	NPD6008	Approved
0.6186	Remote Similarity	NPD5692	Phase 3
0.618	Remote Similarity	NPD5776	Phase 2
0.618	Remote Similarity	NPD6925	Approved
0.618	Remote Similarity	NPD6932	Approved
0.6176	Remote Similarity	NPD5285	Approved
0.6176	Remote Similarity	NPD6648	Approved
0.6176	Remote Similarity	NPD5286	Approved
0.6176	Remote Similarity	NPD4696	Approved
0.617	Remote Similarity	NPD6893	Approved
0.617	Remote Similarity	NPD5363	Approved
0.6168	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD7150	Approved
0.6163	Remote Similarity	NPD6081	Approved
0.6163	Remote Similarity	NPD5777	Approved
0.6163	Remote Similarity	NPD7152	Approved
0.6163	Remote Similarity	NPD7151	Approved
0.6162	Remote Similarity	NPD5282	Discontinued
0.6162	Remote Similarity	NPD6001	Approved
0.6161	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD4252	Approved
0.6145	Remote Similarity	NPD4224	Phase 2
0.6139	Remote Similarity	NPD4755	Approved
0.6132	Remote Similarity	NPD6412	Phase 2
0.6129	Remote Similarity	NPD3669	Approved
0.6129	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7983	Approved
0.6118	Remote Similarity	NPD6923	Approved
0.6118	Remote Similarity	NPD6922	Approved
0.6117	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD6114	Approved
0.6111	Remote Similarity	NPD6697	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