NPASS Compound

Structure

NPC476431 OpenBabel07101719242D 21 22 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 0.8660 1.5000 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 3.4641 -1.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 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 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 15 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 19 5 1 6 0 0 0 20 6 1 6 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.26
Volume:	340.881
LogP:	5.754
LogD:	4.489
LogS:	-5.452
# Rotatable Bonds:	3
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	4.286
Fsp3:	0.8
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:	-4.423
MDCK Permeability:	1.0690262570278719e-05
Pgp-inhibitor:	0.213
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	95.81703186035156%
Volume Distribution (VD):	1.598
Pgp-substrate:	2.8000051975250244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.176
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.568
CYP3A4-substrate:	0.575

ADMET: Excretion

Clearance (CL):	12.007
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.518
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.202
Skin Sensitization:	0.483
Carcinogencity:	0.464
Eye Corrosion:	0.946
Eye Irritation:	0.882
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC476431

Natural Product ID:	NPC476431
*Common Name:**	(8Alpha,12Z)-12,14-Labdadien-8-Ol
IUPAC Name:	(2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[(2Z)-3-methylpenta-2,4-dienyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	ZAZVCYBIABTSJR-YTUHAPFPSA-N
Standard InCHI:	InChI=1S/C20H34O/c1-7-15(2)9-10-17-19(5)13-8-12-18(3,4)16(19)11-14-20(17,6)21/h7,9,16-17,21H,1,8,10-14H2,2-6H3/b15-9-/t16-,17?,19-,20+/m0/s1
SMILES:	CC(=CCC1C2(CCCC(C2CCC1(C)O)(C)C)C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL603753
PubChem CID:	16725072
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
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	20.3	ug.mL-1	PMID[502732]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[502732]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25.0	ug.mL-1	PMID[502732]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[502732]

☑ 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 NPC476431 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	187
0.1-0.2	1521
0.2-0.3	6779
0.3-0.4	17348
0.4-0.5	8524
0.5-0.6	5532
0.6-0.7	2226
0.7-0.8	513
0.8-0.85	50
0.85-0.9	15
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC64123
0.9242	High Similarity	NPC94192
0.8841	High Similarity	NPC167706
0.8714	High Similarity	NPC68443
0.8714	High Similarity	NPC182717
0.8657	High Similarity	NPC149680
0.8657	High Similarity	NPC279434
0.8615	High Similarity	NPC282694
0.8615	High Similarity	NPC79576
0.8615	High Similarity	NPC194208
0.8611	High Similarity	NPC106432
0.8592	High Similarity	NPC201048
0.8592	High Similarity	NPC476366
0.8438	Intermediate Similarity	NPC474769
0.8438	Intermediate Similarity	NPC189290
0.8429	Intermediate Similarity	NPC475728
0.8406	Intermediate Similarity	NPC32055
0.8356	Intermediate Similarity	NPC470749
0.8356	Intermediate Similarity	NPC265588
0.8333	Intermediate Similarity	NPC477138
0.8333	Intermediate Similarity	NPC100334
0.8333	Intermediate Similarity	NPC91858
0.8333	Intermediate Similarity	NPC22134
0.8333	Intermediate Similarity	NPC41160
0.8333	Intermediate Similarity	NPC243342
0.831	Intermediate Similarity	NPC110799
0.8261	Intermediate Similarity	NPC197805
0.8261	Intermediate Similarity	NPC117607
0.8261	Intermediate Similarity	NPC101307
0.8261	Intermediate Similarity	NPC88454
0.8243	Intermediate Similarity	NPC470711
0.8243	Intermediate Similarity	NPC470758
0.8243	Intermediate Similarity	NPC471798
0.8219	Intermediate Similarity	NPC291503
0.8219	Intermediate Similarity	NPC32832
0.8205	Intermediate Similarity	NPC474493
0.8194	Intermediate Similarity	NPC471799
0.8169	Intermediate Similarity	NPC145498
0.8143	Intermediate Similarity	NPC208999
0.8143	Intermediate Similarity	NPC2648
0.8143	Intermediate Similarity	NPC216460
0.8133	Intermediate Similarity	NPC318136
0.8133	Intermediate Similarity	NPC18603
0.8133	Intermediate Similarity	NPC307965
0.8133	Intermediate Similarity	NPC186191
0.8133	Intermediate Similarity	NPC76931
0.8133	Intermediate Similarity	NPC285761
0.8133	Intermediate Similarity	NPC205455
0.8133	Intermediate Similarity	NPC72507
0.8125	Intermediate Similarity	NPC39068
0.8125	Intermediate Similarity	NPC264779
0.8116	Intermediate Similarity	NPC222366
0.8116	Intermediate Similarity	NPC476039
0.8116	Intermediate Similarity	NPC286669
0.8108	Intermediate Similarity	NPC30590
0.8108	Intermediate Similarity	NPC122418
0.8108	Intermediate Similarity	NPC265328
0.8108	Intermediate Similarity	NPC129165
0.8108	Intermediate Similarity	NPC134330
0.8108	Intermediate Similarity	NPC189883
0.8108	Intermediate Similarity	NPC290598
0.8108	Intermediate Similarity	NPC63958
0.8108	Intermediate Similarity	NPC120098
0.8108	Intermediate Similarity	NPC237460
0.8108	Intermediate Similarity	NPC27765
0.8088	Intermediate Similarity	NPC225415
0.8082	Intermediate Similarity	NPC471797
0.8077	Intermediate Similarity	NPC82538
0.8077	Intermediate Similarity	NPC237795
0.8056	Intermediate Similarity	NPC242001
0.8056	Intermediate Similarity	NPC164022
0.8028	Intermediate Similarity	NPC9942
0.8028	Intermediate Similarity	NPC210323
0.8026	Intermediate Similarity	NPC80530
0.8026	Intermediate Similarity	NPC291379
0.8026	Intermediate Similarity	NPC273410
0.8	Intermediate Similarity	NPC472805
0.8	Intermediate Similarity	NPC91594
0.8	Intermediate Similarity	NPC132542
0.8	Intermediate Similarity	NPC40394
0.8	Intermediate Similarity	NPC101475
0.8	Intermediate Similarity	NPC157996
0.8	Intermediate Similarity	NPC34177
0.8	Intermediate Similarity	NPC90979
0.7975	Intermediate Similarity	NPC231310
0.7973	Intermediate Similarity	NPC471723
0.7973	Intermediate Similarity	NPC66566
0.7973	Intermediate Similarity	NPC477923
0.7973	Intermediate Similarity	NPC257347
0.7973	Intermediate Similarity	NPC138374
0.7973	Intermediate Similarity	NPC34700
0.7973	Intermediate Similarity	NPC141071
0.7949	Intermediate Similarity	NPC296701
0.7949	Intermediate Similarity	NPC218616
0.7941	Intermediate Similarity	NPC174956
0.7941	Intermediate Similarity	NPC81615
0.7922	Intermediate Similarity	NPC102253
0.7922	Intermediate Similarity	NPC13554
0.7922	Intermediate Similarity	NPC322313
0.7922	Intermediate Similarity	NPC236237
0.7917	Intermediate Similarity	NPC92801
0.791	Intermediate Similarity	NPC176621
0.7895	Intermediate Similarity	NPC158662
0.7895	Intermediate Similarity	NPC253807
0.7895	Intermediate Similarity	NPC98386
0.7895	Intermediate Similarity	NPC167037
0.7895	Intermediate Similarity	NPC470396
0.7895	Intermediate Similarity	NPC65897
0.7895	Intermediate Similarity	NPC138621
0.7895	Intermediate Similarity	NPC302041
0.7895	Intermediate Similarity	NPC244385
0.7895	Intermediate Similarity	NPC196753
0.7895	Intermediate Similarity	NPC474989
0.7895	Intermediate Similarity	NPC312328
0.7895	Intermediate Similarity	NPC11908
0.7895	Intermediate Similarity	NPC22955
0.7895	Intermediate Similarity	NPC85346
0.7895	Intermediate Similarity	NPC300499
0.7895	Intermediate Similarity	NPC99168
0.7895	Intermediate Similarity	NPC230295
0.7895	Intermediate Similarity	NPC6978
0.7887	Intermediate Similarity	NPC139785
0.7887	Intermediate Similarity	NPC160209
0.7867	Intermediate Similarity	NPC202642
0.7867	Intermediate Similarity	NPC113733
0.7867	Intermediate Similarity	NPC106364
0.7867	Intermediate Similarity	NPC300324
0.7867	Intermediate Similarity	NPC470362
0.7867	Intermediate Similarity	NPC46160
0.7867	Intermediate Similarity	NPC240604
0.7857	Intermediate Similarity	NPC476406
0.7848	Intermediate Similarity	NPC474789
0.7848	Intermediate Similarity	NPC52108
0.7846	Intermediate Similarity	NPC179024
0.7838	Intermediate Similarity	NPC306727
0.7838	Intermediate Similarity	NPC27395
0.7838	Intermediate Similarity	NPC329090
0.7826	Intermediate Similarity	NPC101128
0.7821	Intermediate Similarity	NPC6707
0.7821	Intermediate Similarity	NPC476646
0.7821	Intermediate Similarity	NPC70927
0.7821	Intermediate Similarity	NPC473217
0.7821	Intermediate Similarity	NPC249423
0.7794	Intermediate Similarity	NPC469728
0.7792	Intermediate Similarity	NPC53744
0.7792	Intermediate Similarity	NPC1319
0.7792	Intermediate Similarity	NPC472463
0.7792	Intermediate Similarity	NPC129501
0.7763	Intermediate Similarity	NPC130136
0.7763	Intermediate Similarity	NPC214570
0.7763	Intermediate Similarity	NPC198968
0.7763	Intermediate Similarity	NPC155986
0.7763	Intermediate Similarity	NPC318495
0.7763	Intermediate Similarity	NPC477924
0.775	Intermediate Similarity	NPC238485
0.775	Intermediate Similarity	NPC470077
0.7746	Intermediate Similarity	NPC269077
0.7746	Intermediate Similarity	NPC69649
0.7746	Intermediate Similarity	NPC68703
0.7746	Intermediate Similarity	NPC253303
0.7746	Intermediate Similarity	NPC185874
0.7746	Intermediate Similarity	NPC139207
0.7733	Intermediate Similarity	NPC22105
0.7733	Intermediate Similarity	NPC118508
0.7733	Intermediate Similarity	NPC476844
0.7733	Intermediate Similarity	NPC134847
0.7733	Intermediate Similarity	NPC304309
0.7733	Intermediate Similarity	NPC328104
0.7733	Intermediate Similarity	NPC319090
0.7733	Intermediate Similarity	NPC471468
0.7733	Intermediate Similarity	NPC230301
0.7733	Intermediate Similarity	NPC121744
0.7733	Intermediate Similarity	NPC288035
0.7733	Intermediate Similarity	NPC136188
0.7733	Intermediate Similarity	NPC322353
0.7733	Intermediate Similarity	NPC285893
0.7733	Intermediate Similarity	NPC162742
0.7733	Intermediate Similarity	NPC28657
0.7722	Intermediate Similarity	NPC30166
0.7722	Intermediate Similarity	NPC155521
0.7722	Intermediate Similarity	NPC201852
0.7722	Intermediate Similarity	NPC2524
0.7722	Intermediate Similarity	NPC49964
0.7722	Intermediate Similarity	NPC87489
0.7722	Intermediate Similarity	NPC20853
0.7722	Intermediate Similarity	NPC202389
0.7714	Intermediate Similarity	NPC258595
0.7714	Intermediate Similarity	NPC163678
0.7703	Intermediate Similarity	NPC130665
0.7692	Intermediate Similarity	NPC236112
0.7692	Intermediate Similarity	NPC241290
0.7692	Intermediate Similarity	NPC164840
0.7692	Intermediate Similarity	NPC96362
0.7692	Intermediate Similarity	NPC295131
0.7692	Intermediate Similarity	NPC476809
0.7692	Intermediate Similarity	NPC209944
0.7692	Intermediate Similarity	NPC287749
0.7683	Intermediate Similarity	NPC141292
0.7671	Intermediate Similarity	NPC49422
0.7671	Intermediate Similarity	NPC9161

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 NPC476431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1634
0.2-0.3	4132
0.3-0.4	2277
0.4-0.5	552
0.5-0.6	238
0.6-0.7	92
0.7-0.8	27
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
0.8082	Intermediate Similarity	NPD4785	Approved
0.8082	Intermediate Similarity	NPD4784	Approved
0.8056	Intermediate Similarity	NPD4243	Approved
0.7922	Intermediate Similarity	NPD7525	Registered
0.7838	Intermediate Similarity	NPD6924	Approved
0.7838	Intermediate Similarity	NPD6926	Approved
0.7808	Intermediate Similarity	NPD7152	Approved
0.7808	Intermediate Similarity	NPD7150	Approved
0.7808	Intermediate Similarity	NPD7151	Approved
0.7792	Intermediate Similarity	NPD7645	Phase 2
0.7733	Intermediate Similarity	NPD7339	Approved
0.7733	Intermediate Similarity	NPD6942	Approved
0.7671	Intermediate Similarity	NPD7143	Approved
0.7671	Intermediate Similarity	NPD7144	Approved
0.7632	Intermediate Similarity	NPD6933	Approved
0.7534	Intermediate Similarity	NPD6923	Approved
0.7534	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.75	Intermediate Similarity	NPD5275	Approved
0.75	Intermediate Similarity	NPD4190	Phase 3
0.7468	Intermediate Similarity	NPD7509	Discontinued
0.7403	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4195	Approved
0.7308	Intermediate Similarity	NPD6932	Approved
0.725	Intermediate Similarity	NPD6930	Phase 2
0.725	Intermediate Similarity	NPD6931	Approved
0.7215	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6929	Approved
0.7037	Intermediate Similarity	NPD7514	Phase 3
0.7037	Intermediate Similarity	NPD7332	Phase 2
0.7	Intermediate Similarity	NPD7145	Approved
0.6988	Remote Similarity	NPD6695	Phase 3
0.6941	Remote Similarity	NPD3618	Phase 1
0.6932	Remote Similarity	NPD6079	Approved
0.6914	Remote Similarity	NPD6683	Phase 2
0.6905	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD5776	Phase 2
0.6867	Remote Similarity	NPD3667	Approved
0.6867	Remote Similarity	NPD4223	Phase 3
0.6867	Remote Similarity	NPD4221	Approved
0.6824	Remote Similarity	NPD6893	Approved
0.6824	Remote Similarity	NPD5329	Approved
0.6747	Remote Similarity	NPD6898	Phase 1
0.6747	Remote Similarity	NPD6902	Approved
0.6744	Remote Similarity	NPD4519	Discontinued
0.6744	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4694	Approved
0.6744	Remote Similarity	NPD4623	Approved
0.6744	Remote Similarity	NPD5280	Approved
0.6742	Remote Similarity	NPD7515	Phase 2
0.6706	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6627	Remote Similarity	NPD4748	Discontinued
0.6627	Remote Similarity	NPD4695	Discontinued
0.6593	Remote Similarity	NPD7748	Approved
0.6556	Remote Similarity	NPD5284	Approved
0.6556	Remote Similarity	NPD5281	Approved
0.6552	Remote Similarity	NPD4138	Approved
0.6552	Remote Similarity	NPD4689	Approved
0.6552	Remote Similarity	NPD4693	Phase 3
0.6552	Remote Similarity	NPD5690	Phase 2
0.6552	Remote Similarity	NPD4690	Approved
0.6552	Remote Similarity	NPD5205	Approved
0.6552	Remote Similarity	NPD4688	Approved
0.6517	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3666	Approved
0.6512	Remote Similarity	NPD3665	Phase 1
0.6512	Remote Similarity	NPD3133	Approved
0.6452	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5286	Approved
0.6421	Remote Similarity	NPD5285	Approved
0.6421	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD4723	Approved
0.6404	Remote Similarity	NPD4722	Approved
0.6386	Remote Similarity	NPD3617	Approved
0.6383	Remote Similarity	NPD7902	Approved
0.6383	Remote Similarity	NPD4755	Approved
0.6383	Remote Similarity	NPD5173	Approved
0.6374	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD5279	Phase 3
0.6354	Remote Similarity	NPD5223	Approved
0.6351	Remote Similarity	NPD368	Approved
0.6338	Remote Similarity	NPD4219	Approved
0.6333	Remote Similarity	NPD4753	Phase 2
0.6322	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD5290	Discontinued
0.6316	Remote Similarity	NPD7638	Approved
0.6304	Remote Similarity	NPD6399	Phase 3
0.6296	Remote Similarity	NPD4058	Approved
0.6289	Remote Similarity	NPD5211	Phase 2
0.6289	Remote Similarity	NPD5225	Approved
0.6289	Remote Similarity	NPD5226	Approved
0.6289	Remote Similarity	NPD4633	Approved
0.6289	Remote Similarity	NPD5224	Approved
0.6277	Remote Similarity	NPD4697	Phase 3
0.6269	Remote Similarity	NPD8262	Approved
0.6264	Remote Similarity	NPD4096	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.625	Remote Similarity	NPD4700	Approved
0.6235	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5174	Approved
0.6224	Remote Similarity	NPD5175	Approved
0.6222	Remote Similarity	NPD4518	Approved
0.6207	Remote Similarity	NPD4788	Approved
0.6203	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD342	Phase 1
0.6196	Remote Similarity	NPD6411	Approved
0.618	Remote Similarity	NPD6098	Approved
0.617	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD5210	Approved
0.6163	Remote Similarity	NPD4139	Approved
0.6163	Remote Similarity	NPD4692	Approved
0.6162	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD6881	Approved
0.6139	Remote Similarity	NPD6899	Approved
0.6129	Remote Similarity	NPD5133	Approved
0.61	Remote Similarity	NPD5739	Approved
0.61	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD7128	Approved
0.61	Remote Similarity	NPD6675	Approved
0.6098	Remote Similarity	NPD5733	Approved
0.6098	Remote Similarity	NPD4687	Approved
0.6094	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD7136	Phase 2
0.6076	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD5360	Phase 3
0.6076	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD1696	Phase 3
0.6064	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7900	Approved
0.6061	Remote Similarity	NPD4754	Approved
0.6042	Remote Similarity	NPD6083	Phase 2
0.6042	Remote Similarity	NPD6084	Phase 2
0.604	Remote Similarity	NPD5697	Approved
0.6026	Remote Similarity	NPD7331	Phase 2
0.6022	Remote Similarity	NPD8035	Phase 2
0.6022	Remote Similarity	NPD8034	Phase 2
0.6022	Remote Similarity	NPD6050	Approved
0.6022	Remote Similarity	NPD7637	Suspended
0.6022	Remote Similarity	NPD5694	Approved
0.6019	Remote Similarity	NPD7102	Approved
0.6019	Remote Similarity	NPD7290	Approved
0.6019	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4729	Approved
0.598	Remote Similarity	NPD6011	Approved
0.598	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD4730	Approved
0.5979	Remote Similarity	NPD4225	Approved
0.5978	Remote Similarity	NPD6051	Approved
0.5978	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6673	Approved
0.5978	Remote Similarity	NPD6904	Approved
0.5978	Remote Similarity	NPD6080	Approved
0.5976	Remote Similarity	NPD4732	Discontinued
0.5962	Remote Similarity	NPD8130	Phase 1
0.5962	Remote Similarity	NPD6650	Approved
0.5962	Remote Similarity	NPD6617	Approved
0.5962	Remote Similarity	NPD6847	Approved
0.5962	Remote Similarity	NPD6649	Approved
0.5962	Remote Similarity	NPD6869	Approved
0.5941	Remote Similarity	NPD4768	Approved
0.5941	Remote Similarity	NPD4767	Approved
0.5926	Remote Similarity	NPD4747	Approved
0.5926	Remote Similarity	NPD4787	Phase 1
0.5926	Remote Similarity	NPD4691	Approved
0.5922	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD6014	Approved
0.5922	Remote Similarity	NPD6013	Approved
0.5922	Remote Similarity	NPD6373	Approved
0.5921	Remote Similarity	NPD4194	Approved
0.5921	Remote Similarity	NPD4191	Approved
0.5921	Remote Similarity	NPD4193	Approved
0.5921	Remote Similarity	NPD4192	Approved
0.5914	Remote Similarity	NPD5692	Phase 3
0.5905	Remote Similarity	NPD6882	Approved
0.5905	Remote Similarity	NPD8297	Approved
0.5897	Remote Similarity	NPD7341	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