NPASS Compound

Structure

NPC323349 OpenBabel06302215202D 44 47 0 0 1 0 0 0 0 0999 V2000 -3.2053 -2.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0713 -1.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9373 -2.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8034 -1.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6694 -2.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5354 -1.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5354 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6694 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4014 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2675 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1335 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1335 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2675 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9995 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8655 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7316 1.4659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -12.7316 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5976 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4636 0.4659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -14.4636 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5976 1.9659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -12.7316 2.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.4636 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.3296 -0.0341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2316 -0.4001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7316 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0713 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2053 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3393 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4732 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4732 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5176 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 1.4836 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9319 0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1566 1.7424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 3 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 3 0 0 0 5 6 1 0 0 0 0 6 7 2 3 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 9 10 2 3 0 0 0 10 11 1 0 0 0 0 11 12 2 3 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 15 2 3 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 27 28 2 3 0 0 0 28 29 1 0 0 0 0 29 30 2 3 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 32 33 2 3 0 0 0 33 34 1 0 0 0 0 34 39 1 0 0 0 0 34 40 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 35 43 1 0 0 0 0 35 44 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 37 42 1 0 0 0 0 38 39 1 0 0 0 0 39 40 1 0 0 0 0 39 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.42
Volume:	677.603
LogP:	7.973
LogD:	5.449
LogS:	-6.54
# Rotatable Bonds:	10
TPSA:	65.52
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.194
Synthetic Accessibility Score:	5.425
Fsp3:	0.55
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.144
MDCK Permeability:	1.9287012037239037e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.679
20% Bioavailability (F20%):	0.41
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	97.4292221069336%
Volume Distribution (VD):	2.8
Pgp-substrate:	2.9405343532562256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.208
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.537
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.772
CYP3A4-substrate:	0.96

ADMET: Excretion

Clearance (CL):	5.061
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.757
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.0
AMES Toxicity:	0.225
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.981
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.699

Download Data

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

Natural Product: NPC323349

Natural Product ID:	NPC323349
*Common Name:**	SZCBXWMUOPQSOX-DKLMTRRASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SZCBXWMUOPQSOX-DKLMTRRASA-N
Standard InCHI:	InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
SMILES:	CC(=CC=CC=C(C)C=CC=C(C)C=CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=CC34C(CC(CC3(O4)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	6384269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001410] Xanthophylls

*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
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22305790]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[25539472]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31351	Spirodela polyrrhiza	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27261	Carica papaya	Species	Caricaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC323349 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Natural Product ID

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 NPC323349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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